GB918970A - Dihalomethylene diamines - Google Patents
Dihalomethylene diaminesInfo
- Publication number
- GB918970A GB918970A GB209161A GB209161A GB918970A GB 918970 A GB918970 A GB 918970A GB 209161 A GB209161 A GB 209161A GB 209161 A GB209161 A GB 209161A GB 918970 A GB918970 A GB 918970A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dimethyl
- dichloromethylene
- diamine
- reacting
- phenyl
- 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.)
- Expired
Links
- 150000004985 diamines Chemical class 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 4
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 2
- 150000005840 aryl radicals Chemical class 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Chemical group 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 2
- -1 chlorophenyl radical Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- OGFAWKRXZLGJSK-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone Chemical compound OC1=CC(O)=CC=C1C(=O)CC1=CC=C([N+]([O-])=O)C=C1 OGFAWKRXZLGJSK-UHFFFAOYSA-N 0.000 abstract 1
- 239000005995 Aluminium silicate Substances 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 235000012211 aluminium silicate Nutrition 0.000 abstract 1
- 239000004202 carbamide Substances 0.000 abstract 1
- 230000002363 herbicidal effect Effects 0.000 abstract 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- 239000000454 talc Substances 0.000 abstract 1
- 229910052623 talc Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/74—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by halogenation, hydrohalogenation, dehalogenation, or dehydrohalogenation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention comprises dihalomethylene diamines of formula <FORM:0918970/IV (b)/1> where R1 is a phenyl or chlorophenyl radical, R2, R3 and R4 are hydrogen atoms or alkyl or aryl radicals, and X is chlorine or bromine. The compounds are prepared by reacting a corresponding urea of formula <FORM:0918970/IV (b)/2> with phosphorus pentachloride or pentabromide, or by reacting an a -haloformamidine of formula <FORM:0918970/IV (b)/3> with hydrogen chloride or hydrogen bromide. In examples N-(4-chlorophenyl)-N,N1-dimethyl dichloromethylene diamine is prepared by reacting N - (4 - chlorophenyl) - N,N1 - dimethyl urea with phosphorus pentachloride, and N-phenyl-N,N1-dimethyl dichloromethylene diamine is prepared by reacting N-phenyl-N,N1-dimethyl urea with phosphorus pentachloride. Other compounds are mentioned. Specifications 874,928 and 888,646 are referred to.ALSO:Herbicidal compositions contain dihalomethylene diamines of formula <FORM:0918970/VI/1> where R1 is an unsubstituted or substituted aromatic radical, R2, R3 and R4 are hydrogen atoms or unsubstituted or substituted alkyl or aryl radicals, and X is chlorine or bromine. The composition may include an inert carrier, e.g. talc or kaolin. Compounds specified in examples are N - (4 - chlorophenyl) - N, N1 - dimethyl dichloromethylene diamine and N-phenyl - N, N1 - dimethyl dichloromethylene diamine. Other compounds are mentioned. Specifications 874,928 and 888,646 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF30339A DE1129161B (en) | 1960-01-19 | 1960-01-19 | Process for the preparation of dihalomethylenediamines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB918970A true GB918970A (en) | 1963-02-20 |
Family
ID=7093729
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB209161A Expired GB918970A (en) | 1960-01-19 | 1961-01-18 | Dihalomethylene diamines |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH390268A (en) |
| DE (1) | DE1129161B (en) |
| GB (1) | GB918970A (en) |
-
1960
- 1960-01-19 DE DEF30339A patent/DE1129161B/en active Pending
-
1961
- 1961-01-06 CH CH16661A patent/CH390268A/en unknown
- 1961-01-18 GB GB209161A patent/GB918970A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1129161B (en) | 1962-05-10 |
| CH390268A (en) | 1965-04-15 |
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