DE1094737B - Process for the preparation of aryl isocyanide dihalides - Google Patents
Process for the preparation of aryl isocyanide dihalidesInfo
- Publication number
- DE1094737B DE1094737B DEF28552A DEF0028552A DE1094737B DE 1094737 B DE1094737 B DE 1094737B DE F28552 A DEF28552 A DE F28552A DE F0028552 A DEF0028552 A DE F0028552A DE 1094737 B DE1094737 B DE 1094737B
- Authority
- DE
- Germany
- Prior art keywords
- aryl
- preparation
- ccl
- thionyl chloride
- aryl isocyanide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- -1 aryl isocyanide Chemical compound 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 24
- 239000000460 chlorine Substances 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 230000002140 halogenating effect Effects 0.000 claims description 4
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000005660 chlorination reaction Methods 0.000 description 3
- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 3
- LMLFHXMNNHGRRO-UHFFFAOYSA-N n-(4-chlorophenyl)formamide Chemical compound ClC1=CC=C(NC=O)C=C1 LMLFHXMNNHGRRO-UHFFFAOYSA-N 0.000 description 3
- ZFULXOGYCDBCHD-UHFFFAOYSA-N (4-chlorophenyl)-methylidyneazanium Chemical compound ClC1=CC=C([N+]#C)C=C1 ZFULXOGYCDBCHD-UHFFFAOYSA-N 0.000 description 2
- PCVRZLUZDSRYDM-UHFFFAOYSA-N 1,2-dichloro-3-isocyanobenzene Chemical compound ClC1=CC=CC([N+]#[C-])=C1Cl PCVRZLUZDSRYDM-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- WTKFBCXCSGVNOE-UHFFFAOYSA-N n-(3,4-dichlorophenyl)formamide Chemical compound ClC1=CC=C(NC=O)C=C1Cl WTKFBCXCSGVNOE-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 2
- TTWWZVGVBRPHLE-UHFFFAOYSA-N 1,1-dichloro-n-phenylmethanimine Chemical compound ClC(Cl)=NC1=CC=CC=C1 TTWWZVGVBRPHLE-UHFFFAOYSA-N 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- 241000219193 Brassicaceae Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- SXEVZVMJNXOXIJ-UHFFFAOYSA-N n-(4-methoxyphenyl)formamide Chemical compound COC1=CC=C(NC=O)C=C1 SXEVZVMJNXOXIJ-UHFFFAOYSA-N 0.000 description 1
- ZTCQFVRINYOPOH-UHFFFAOYSA-N n-(4-nitrophenyl)formamide Chemical compound [O-][N+](=O)C1=CC=C(NC=O)C=C1 ZTCQFVRINYOPOH-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
DEUTSCHESGERMAN
Aryl-isocyanid-dihalogenide sind in der Literatur bereits vereinzelt beschrieben worden. So läßt sich Phenylisocyanid-dichlorid nach den Angaben in Ber., 7, S. 1228, durch Chlorierung von Phenylsenföl in relativ guter Ausbeute herstellen. Jedoch entsteht bei diesem Verfahren stets Schwefeldichlorid als lästiges Nebenprodukt entsprechend nachfolgendem Formelschema:Aryl isocyanide dihalides have already been described in isolated cases in the literature. So can phenyl isocyanide dichloride according to the information in Ber., 7, p. 1228, by chlorination of phenyl mustard oil in relatively good yield produce. However, this process always produces sulfur dichloride as an annoying by-product following formula scheme:
Verfahren zur Herstellung
von Aryl-isocyanid-dihalogenidenMethod of manufacture
of aryl isocyanide dihalides
Dieses Verfahren läßt sich aber bei kernsubstituierten Arylsenfölen nicht mehr so glatt durchführen, da hierbei Nebenreaktionen (Kernchlorierung, Bildung dimerer Anlagerungsverbindungen) auftreten.In the case of ring-substituted aryl mustards, however, this process can no longer be carried out as smoothly as it does Side reactions (nuclear chlorination, formation of dimeric addition compounds) occur.
Die Anlagerung von Halogen an Aryl-isocyanide verläuft zwar glatt, doch ist der Umgang mit den giftigen und übelriechenden sowie relativ instabilen Aryl-isocyaniden in der Praxis ein Nachteil.The addition of halogen to aryl isocyanides takes place Although smooth, the handling of the poisonous and foul-smelling as well as relatively unstable aryl isocyanides is easy a disadvantage in practice.
Aus der Literatur (Am. Soc, 44, S. 2896) ist weiter bekannt, daß bei der Chlorierung von Formylanilin in Chloroform in Gegenwart von Thionylchlorid ein Gemisch von Phenyl-, p-Chlorphenyl-, Dichlorphenyl-isocyaniddichlorid und 2,4-Dichlorformanilid entsteht.From the literature (Am. Soc, 44, p. 2896) it is also known that in the chlorination of formylaniline in Chloroform in the presence of thionyl chloride, a mixture of phenyl, p-chlorophenyl, dichlorophenyl isocyanide dichloride and 2,4-dichloroformanilide is formed.
Es wurde nun gefunden, daß man überraschenderweise in einheitlicher Reaktion und in sehr guten Ausbeuten Aryl-isocyanid-dihalogenide erhält, wenn man ein beliebiges N-Arylformamid in überschüssigem Thionylchlorid und Thionylbromid mit der benötigten Menge Chlor oder Brom oder eines sonstigen Halogenierungsmittels wie Sulfurylchlorid versetzt. Man arbeitet dabei zweckmäßigerweise bei einer Temperatur unterhalb 25° C. Das im Überschuß verwendete Thionylchlorid bzw. Thionylbromid kann nach der Reaktion durch Destillation abgetrennt und für weitere Ansätze erneut eingesetzt werden.It has now been found that, surprisingly, in a uniform reaction and in very good yields Aryl isocyanide dihalides are obtained if any N-arylformamide is used in excess thionyl chloride and thionyl bromide with the required amount of chlorine or bromine or another halogenating agent like sulfuryl chloride added. It is expedient to work at a temperature below 25 ° C. The thionyl chloride or thionyl bromide used in excess can after the reaction Separated distillation and used again for further approaches.
Die entstehenden Aryl-isocyanid-dihalogenide sind im allgemeinen farblose oder leichtgelbgefärbte Öle und können durch Destillation gereinigt werden.The resulting aryl isocyanide dihalides are generally colorless or pale yellow oils and can be purified by distillation.
Für die erfindungsgemäße Reaktion geeignete Arylformamide sind z. B. Formylanilin, Formyltoluidine, halogenierte Arylformamide, wie N-(4-Chlorphenyl)-formamid, N-(3,4-Dichlorphenyl)-formamid, N-(4-Nitrophenyl) - formamid, N - (4 - Methoxyphenyl) - formamid und N-(a-Naphthyl)-formamid, Arylformamide mit Sulfon- oder substituierten Sulfonamidgruppen, Bisformamide, die sich von Phenylendiaminen, Benzidin und seinen Derivaten ableiten, u. dgl.Arylformamides suitable for the reaction according to the invention are z. B. formylaniline, formyltoluidines, halogenated arylformamides, such as N- (4-chlorophenyl) formamide, N- (3,4-dichlorophenyl) formamide, N- (4-nitrophenyl) formamide, N - (4 - methoxyphenyl) formamide and N- (a-naphthyl) -formamide, arylformamides with sulfonic or substituted sulfonamide groups, bisformamides, derived from phenylenediamines, benzidine and its derivatives, and the like.
Die Aryl-isocyanid-dihalogenide sind wertvolle Zwischenprodukte für weitere Synthesen, vor allem auf dem Pflanzenschutz- und Heilmittelsektor.The aryl isocyanide dihalides are valuable intermediates for further syntheses, especially on the Plant protection and medicinal products sector.
77,5 g N-(p-Chlorphenyl)-formamid werden unterhalb 10° C in eine Lösung von 67,5 g Sulfurylchlorid in 150 ml Anmelder:77.5 g of N- (p-chlorophenyl) formamide are dissolved below 10 ° C. in a solution of 67.5 g of sulfuryl chloride in 150 ml Applicant:
ίο Farbenfabriken Bayer Aktiengesellschaft, Leverkusen-Bayerwerkίο paint factories Bayer Aktiengesellschaft, Leverkusen-Bayerwerk
Dr. Engelbert Kühle, Köln-Stammheim,
ist als Erfinder genannt wordenDr. Engelbert Kühle, Cologne-Stammheim,
has been named as the inventor
Thionylchlorid eingetragen. Nach kurzer Zeit entsteht ein dicker Kristallbrei, der sich allmählich wieder verflüssigt. Zur Vervollständigung der HCI- und SO2-Abspaltung rührt man etwa 10 bis 15 Stunden bei Zimmertemperatur nach, destilliert das überschüssige Thionylchlorid ab und fraktioniert den Rückstand im Vakuum. Man erhält hierbei 89 g (=86% der Theorie) p-Chlorphenyl-isocyanid-dichlorid vom Siedepunkt Kp.lo = 110 bis 113°C.Thionyl chloride entered. After a short time, a thick crystal pulp is formed, which gradually liquefies again. To complete the elimination of HCl and SO 2, the mixture is subsequently stirred for about 10 to 15 hours at room temperature, the excess thionyl chloride is distilled off and the residue is fractionated in vacuo. In this case we obtain 89 g (= 86% of theory) of p-chlorophenyl-isocyanide dichloride of boiling point Kp. Lo = 110 to 113 ° C.
30 g Formanilid werden unter Eiskühlung bei 5 bis 10° C in eine Lösung von 40 g Brom in 100 ml Thionylchlorid eingerührt. Nach vorübergehender Lösung entsteht ohne nennenswerte Temperaturerhöhung ein dicker Kristallbrei, der sich nach kurzer Zeit wieder verflüssigt. Man rührt 20 Stunden nach, destilliert überschüssiges Thionylchlorid ab und erhält nach einem kurzen Zwischenlauf 30 g (=46% der Theorie) Phenyl-isocyaniddibromid vom Siedepunkt Kp.u = 128 bis 129° C.30 g of formanilide are stirred into a solution of 40 g of bromine in 100 ml of thionyl chloride at 5 to 10 ° C. while cooling with ice. After a temporary dissolution, a thick crystal slurry is formed without any appreciable increase in temperature, which liquefies again after a short time. It is stirred for 20 hours after, distilled off excess thionyl chloride and, after a brief run 30 g (= 46% of theory) phenyl isocyaniddibromid of boiling point Kp. U = 128-129 ° C.
190 g N-(3,4-Dichlorphenyl)-formamid werden unterhalb 10° C in eine Lösung von 135 g Sulfurylchlorid in 500 ml Thionylchlorid eingerührt. Man läßt die Temperatur auf Zimmertemperatur ansteigen, rührt 20 Stunden zur Vertreibung des entstehenden Schwefeldioxyds und Chlorwasserstoffs nach, destilliert das überschüssige Thionylchlorid ab und destilliert den Rückstand im Vakuum. Hierbei erhält man 198 g (= 81 % der Theorie) S^-Dichlorphenyl-isocyanid-dichlorid vom Siedepunkt Kp.29 = 157 bis 162° C.190 g of N- (3,4-dichlorophenyl) formamide are stirred into a solution of 135 g of sulfuryl chloride in 500 ml of thionyl chloride below 10 ° C. The temperature is allowed to rise to room temperature, the mixture is stirred for 20 hours to drive off the sulfur dioxide and hydrogen chloride formed, the excess thionyl chloride is distilled off and the residue is distilled in vacuo. This gives 198 g (= 81% of theory) of S ^ -dichlorophenyl isocyanide dichloride with a boiling point of bp 29 = 157 to 162 ° C.
009 678/520009 678/520
g N-(p-Chlorphenyl)-formamid werden unter Kühlung bei 10 bis 15° C portionsweise im Verlauf von 6 bis Stunden in 3,51 Thionylchlorid eingetragen. Während dieser Zeit werden gleichzeitig etwa 1400 g (theoretisch benötigte Menge) Chlor eingeleitet. Anschließend rührt man noch 4 Stunden nach, destilliert darauf das überschüssige Thionylchlorid ab und fraktioniert den Rückstand (2830 g) im Vakuum. Hierbei erhält man 1845 g (=68% der Theorie) p-Chlorphenyl-isocyanid-dichlorid und als Nachlauf 516 g Dichlorphenyl-isocyanid-dichlorid 5 (Kp.13 = 131 bis 137° C).g of N- (p-chlorophenyl) formamide are introduced into 3.5 l of thionyl chloride in portions over a period of 6 to hours at 10 to 15 ° C. with cooling. During this time, about 1400 g (theoretically required amount) of chlorine are passed in at the same time. The mixture is then stirred for a further 4 hours, the excess thionyl chloride is then distilled off and the residue (2830 g) is fractionated in vacuo. This gives 1845 g (= 68% of theory) of p-chlorophenyl isocyanide dichloride and 516 g of dichlorophenyl isocyanide dichloride 5 (boiling point 13 = 131 to 137 ° C.) as a tail.
Nach dem im Beispiel 1 beschriebenen Verfahren können außerdem noch die folgenden Aryl-isocyaniddihalogenide hergestellt werden:According to the process described in Example 1, the following aryl isocyanide dihalides can also be used getting produced:
ReaktionsproduktReaction product
Reaktionstemperatur Reaction temperature
Kp. bzw. F.Kp. Or F.
Ausbeuteyield
ClCl
ClCl
ClCl
-N = CCl,-N = CCl,
-N = CCl2 -N = CCl 2
= CCl2 = CCl 2
ClCl
ClCl
Cl ClCl Cl
N = CCl2 N = CCl 2
-N = CCl,-N = CCl,
CLC = NCLC = N
ClC-/ N-N =ClC- / N-N =
-N = N-N = N
-N = CCL 10 bis 15°C 15 bis 2O0C 15 bis 200C-N = CCL 10 to 15 ° C 15 to 2O 0 C for 15 to 20 0 C.
35 bis 400C 55 bis 600C 15 bis 2O0C 15 bis 200C 15 bis 200C 20 bis 25° C35 to 40 0 C 55 to 60 0 C 15 to 2O 0 C for 15 to 20 0 C for 15 to 20 0 C 20 to 25 ° C
45 bis 5O0C45 to 5O 0 C
55 bis 6O0C55 to 6O 0 C
104bisl06°C/10mm104 to 06 ° C / 10mm
126bisl32°C/10mm126 to 32 ° C / 10mm
128bisl35°C/12mm128 to 35 ° C / 12mm
162 bis 165°C/16 mm162 to 165 ° C / 16 mm
128bisl29°C/0,6mm128 to 29 ° C / 0.6mm
142bisl49°C/14mm142 to 49 ° C / 14mm
121bisl23°C/10mm121 to 23 ° C / 10mm
104bisll0°C/10mm104 to 11 0 ° C / 10mm
183bisl90°C/14mm183 to 90 ° C / 14mm
F. 93°CM.p. 93 ° C
152 bis 158°C/11 mm152 to 158 ° C / 11 mm
F. 82 bis 84° CM.p. 82 to 84 ° C
86,7%86.7%
85,5%85.5%
78,4%78.4%
81%81%
54%54%
73,5 %73.5%
96,6%96.6%
78,3%78.3%
20%20%
42%42%
49%49%
31% (umkrist.)31% (recryst.)
ι uy4 ίο ι ι uy4 ίο ι
ReaktionsproduktReaction product
Reaktionstemperatur Kp. bzw. F.Reaction temperature Kp. Or F.
Ausbeuteyield
HaC-H a C-
C2H5 C 2 H 5
X-N = CCIgX-N = CCIg
C8 C 8
OgNOgN
N = CCl2 N = CCl 2
ClCl
— N = CCl2 - N = CCl 2
ClCl
Cl-Cl-
S-N = CCl2 SN = CCl 2
H3CH 3 C
X-C(W'X-C (W '
S-N = CCl2 SN = CCl 2
N = CCl2 N = CCl 2
20 bis 25° C20 to 25 ° C
55 bis 6O0C55 to 6O 0 C
55 bis 60°C55 to 60 ° C
55 bis 600C55 to 60 0 C
20 bis 250C20 to 25 0 C
50 bis 6O0C bisl61°C/10mm50 to 6O 0 C bisl61 ° C / 10mm
bis 133°C/O,1 mmup to 133 ° C / O, 1 mm
bis 116°C/11 mmup to 116 ° C / 11 mm
143bisl46°C/10mm143 to 46 ° C / 10mm
170bisl80°C/0,2mm170 to 80 ° C / 0.2mm
210°C/0,3mm210 ° C / 0.3mm
55,6 »/„55.6 »/"
22%22%
86,5%86.5%
81%81%
73,5%73.5%
39%39%
Claims (3)
zeichnet, daß N-Arylformamide in überschüssigem
Thionylchlorid bzw. -bromid mit entsprechenden
Halogenierungsmitteln umgesetzt werden.1. Process for the production of aryl isocyanide dichlorides or dibromides, thereby marked 40
records that N-arylformamides in excess
Thionyl chloride or bromide with corresponding
Halogenating agents are implemented.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF28552A DE1094737B (en) | 1959-05-29 | 1959-05-29 | Process for the preparation of aryl isocyanide dihalides |
| CH555760A CH394156A (en) | 1959-05-29 | 1960-05-16 | Process for the preparation of aryl isocyanide dihalides |
| GB18176/60A GB908733A (en) | 1959-05-29 | 1960-05-23 | Arylisocyanide dihalides |
| BE591300A BE591300A (en) | 1959-05-29 | 1960-05-27 | Process for the preparation of arylisonitrile dihalides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF28552A DE1094737B (en) | 1959-05-29 | 1959-05-29 | Process for the preparation of aryl isocyanide dihalides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1094737B true DE1094737B (en) | 1960-12-15 |
Family
ID=7092932
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF28552A Pending DE1094737B (en) | 1959-05-29 | 1959-05-29 | Process for the preparation of aryl isocyanide dihalides |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE591300A (en) |
| CH (1) | CH394156A (en) |
| DE (1) | DE1094737B (en) |
| GB (1) | GB908733A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3267144A (en) * | 1963-10-28 | 1966-08-16 | Olin Mathieson | Process for preparing selected bis |
| US3322620A (en) * | 1962-08-01 | 1967-05-30 | Bayer Ag | Compositions and methods for controlling fungi with isocyanide dihalides |
| EP0002217A1 (en) * | 1977-11-29 | 1979-06-13 | Bayer Ag | Process for the preparation of tetrachloropyrimidine |
| EP0373810A1 (en) * | 1988-12-10 | 1990-06-20 | Schering Agrochemicals Limited | Preparation of carbamoyl halides |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL301741A (en) * | 1962-12-14 | |||
| GB1052180A (en) * | 1963-12-11 |
-
1959
- 1959-05-29 DE DEF28552A patent/DE1094737B/en active Pending
-
1960
- 1960-05-16 CH CH555760A patent/CH394156A/en unknown
- 1960-05-23 GB GB18176/60A patent/GB908733A/en not_active Expired
- 1960-05-27 BE BE591300A patent/BE591300A/en unknown
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3322620A (en) * | 1962-08-01 | 1967-05-30 | Bayer Ag | Compositions and methods for controlling fungi with isocyanide dihalides |
| US3267144A (en) * | 1963-10-28 | 1966-08-16 | Olin Mathieson | Process for preparing selected bis |
| EP0002217A1 (en) * | 1977-11-29 | 1979-06-13 | Bayer Ag | Process for the preparation of tetrachloropyrimidine |
| EP0011266A1 (en) * | 1977-11-29 | 1980-05-28 | Bayer Ag | 2-Cyano-ethylisocyanide dichloride and a process for its preparation |
| EP0373810A1 (en) * | 1988-12-10 | 1990-06-20 | Schering Agrochemicals Limited | Preparation of carbamoyl halides |
Also Published As
| Publication number | Publication date |
|---|---|
| CH394156A (en) | 1965-06-30 |
| BE591300A (en) | 1960-09-16 |
| GB908733A (en) | 1962-10-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2213865C3 (en) | Process for the preparation of chlorothiazoles | |
| DE1194418B (en) | Process for the production of new dihalogenamino-benzylamines or their acid addition salts with physiologically compatible acids | |
| DE1094737B (en) | Process for the preparation of aryl isocyanide dihalides | |
| DE1109695B (en) | Process for the preparation of substitution products of 2,3-dimercaptoquinoxaline | |
| DE1237553B (en) | Process for the production of an alpha-chloro-acetic acid amide | |
| DE2301207C2 (en) | Process for the preparation of β-haloalkylaminosulfonyl halides | |
| DE957300C (en) | Process for the production of trichloromethylbenzenes halogenated in the core | |
| DE2648054C3 (en) | Process for the preparation of dichloronitroanilines | |
| EP0087701B1 (en) | Process for the preparation of 2-chlorobenzoxazols | |
| CH500221A (en) | N-disubstd-3-amino-1 2-benzisothiazole derivs antimycotic | |
| DE2054342A1 (en) | New 1,2,4-oxdiazoles | |
| DE1163803B (en) | Process for the preparation of 3-aryl-1,1,3,3-tetrachloro-2-aza-propenes | |
| DE2460821A1 (en) | Carboxylic acid fluorides from other halides - by reaction with inorg fluorides in a two phase system | |
| DE976732C (en) | Process for the production of chlorine- and fluorine-containing dimethyl sulfides | |
| AT233551B (en) | Process for the preparation of chlorine-substituted methyl isocyanide dichlorides | |
| DE1298095B (en) | Process for the preparation of bis-halocarbonyl-amines | |
| AT251592B (en) | Process for the production of organic imide chlorides | |
| DE2137649A1 (en) | THIAZOLINONE (2) CARBONIC ACID ESTER | |
| AT228772B (en) | Process for the preparation of new basic substituted malononitriles | |
| DE947370C (en) | Process for the preparation of 4-thionylamino-2-oxy-benzoyl chloride | |
| DE1018054B (en) | Process for the production of thiocarbonic acid alkyl ester chlorides | |
| DE1056606B (en) | Process for the preparation of dialkylphosphinic acid chlorides | |
| CH387616A (en) | Process for the preparation of 2-bromo-3-halo-propene-1 | |
| DE1132912B (en) | Process for the preparation of a trichlorothioacetamide derivative | |
| DE1128431B (en) | Process for the preparation of basic substituted malonic dinitriles |