DK176046B1 - Fremgangsmåde til fremstilling af 5-amino-2,4,6-triiodisophthalsyre-dichlorid ved chlorering med thionylchlorid i nærværelse af en katalysator - Google Patents

Fremgangsmåde til fremstilling af 5-amino-2,4,6-triiodisophthalsyre-dichlorid ved chlorering med thionylchlorid i nærværelse af en katalysator Download PDF

Info

Publication number: DK176046B1
Authority: DK; Denmark
Prior art keywords: amino; process according; triiodisophthalic acid; thionyl chloride; acid dichloride
Prior art date: 1995-05-18

Application number

DK199701303A

Other languages

Danish (da)

English (en)

Other versions

DK130397A (da

Inventor

Graziano Castaldi

Marco Villa

Claudio Pozzoli

Laura Russo

Original Assignee

Bracco Imaging Spa

Priority date (The priority date 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 date listed.)

1995-05-18

Filing date

1996-05-10

Publication date

2006-02-20

1996-05-10 Application filed by Bracco Imaging Spa filed Critical Bracco Imaging Spa

1997-11-17 Publication of DK130397A publication Critical patent/DK130397A/da

2006-02-20 Application granted granted Critical

2006-02-20 Publication of DK176046B1 publication Critical patent/DK176046B1/da

Links

FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 title claims description 42
238000000034 method Methods 0.000 title claims description 25
FBJVWRITWDYUAC-UHFFFAOYSA-N 5-amino-2,4,6-triiodobenzene-1,3-dicarbonyl chloride Chemical compound NC1=C(I)C(C(Cl)=O)=C(I)C(C(Cl)=O)=C1I FBJVWRITWDYUAC-UHFFFAOYSA-N 0.000 title claims description 19
238000002360 preparation method Methods 0.000 title claims description 8
239000003054 catalyst Substances 0.000 title description 7
238000005660 chlorination reaction Methods 0.000 title description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 47
JEZJSNULLBSYHV-UHFFFAOYSA-N 5-amino-2,4,6-triiodobenzene-1,3-dicarboxylic acid Chemical compound NC1=C(I)C(C(O)=O)=C(I)C(C(O)=O)=C1I JEZJSNULLBSYHV-UHFFFAOYSA-N 0.000 claims description 16
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
150000005621 tetraalkylammonium salts Chemical class 0.000 claims description 14
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
239000000203 mixture Substances 0.000 claims description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 5
125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical group 0.000 claims description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
235000019270 ammonium chloride Nutrition 0.000 claims description 2
150000001649 bromium compounds Chemical class 0.000 claims description 2
ROIPBPWWXWOVSW-UHFFFAOYSA-N bromo(chloro)methanesulfonic acid Chemical group OS(=O)(=O)C(Cl)Br ROIPBPWWXWOVSW-UHFFFAOYSA-N 0.000 claims description 2
OGQYPPBGSLZBEG-UHFFFAOYSA-N dimethyl(dioctadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC OGQYPPBGSLZBEG-UHFFFAOYSA-N 0.000 claims description 2
229960004647 iopamidol Drugs 0.000 claims description 2
XQZXYNRDCRIARQ-LURJTMIESA-N iopamidol Chemical compound C[C@H](O)C(=O)NC1=C(I)C(C(=O)NC(CO)CO)=C(I)C(C(=O)NC(CO)CO)=C1I XQZXYNRDCRIARQ-LURJTMIESA-N 0.000 claims description 2
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 2
229940011051 isopropyl acetate Drugs 0.000 claims description 2
SBHRWOBHKASWGU-UHFFFAOYSA-M tridodecyl(methyl)azanium;chloride Chemical class [Cl-].CCCCCCCCCCCC[N+](C)(CCCCCCCCCCCC)CCCCCCCCCCCC SBHRWOBHKASWGU-UHFFFAOYSA-M 0.000 claims description 2
AMDBBAQNWSUWGN-UHFFFAOYSA-N Ioversol Chemical compound OCCN(C(=O)CO)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I AMDBBAQNWSUWGN-UHFFFAOYSA-N 0.000 claims 1
229960004537 ioversol Drugs 0.000 claims 1
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims 1
125000003944 tolyl group Chemical group 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 8
230000003197 catalytic effect Effects 0.000 description 7
238000003786 synthesis reaction Methods 0.000 description 7
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
238000010992 reflux Methods 0.000 description 6
150000001875 compounds Chemical class 0.000 description 5
XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 5
239000000047 product Substances 0.000 description 5
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
238000001816 cooling Methods 0.000 description 4
239000007787 solid Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
238000010533 azeotropic distillation Methods 0.000 description 3
230000008901 benefit Effects 0.000 description 3
239000000193 iodinated contrast media Substances 0.000 description 3
238000002955 isolation Methods 0.000 description 3
238000010626 work up procedure Methods 0.000 description 3
239000006227 byproduct Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
TZEBLZRSPJJCOS-UHFFFAOYSA-N 2,4,6-triiodo-5-(methylamino)benzene-1,3-dicarbonyl chloride Chemical compound CNC1=C(I)C(C(Cl)=O)=C(I)C(C(Cl)=O)=C1I TZEBLZRSPJJCOS-UHFFFAOYSA-N 0.000 description 1
KNDAEDDIIQYRHY-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-(piperazin-1-ylmethyl)pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)CN1CCNCC1 KNDAEDDIIQYRHY-UHFFFAOYSA-N 0.000 description 1
GSFNQBFZFXUTBN-UHFFFAOYSA-N 2-chlorothiophene Chemical compound ClC1=CC=CS1 GSFNQBFZFXUTBN-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
150000001348 alkyl chlorides Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
229960003237 betaine Drugs 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
-1 dichloride 5-amino-2,4,6-triiodisophthalic acid dichloride Chemical compound 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
229960001025 iohexol Drugs 0.000 description 1
NTHXOOBQLCIOLC-UHFFFAOYSA-N iohexol Chemical compound OCC(O)CN(C(=O)C)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I NTHXOOBQLCIOLC-UHFFFAOYSA-N 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
238000002386 leaching Methods 0.000 description 1
TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
ZUZLIXGTXQBUDC-UHFFFAOYSA-N methyltrioctylammonium Chemical compound CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC ZUZLIXGTXQBUDC-UHFFFAOYSA-N 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
125000005490 tosylate group Chemical group 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Indole Compounds (AREA)

DK199701303A 1995-05-18 1996-05-10 Fremgangsmåde til fremstilling af 5-amino-2,4,6-triiodisophthalsyre-dichlorid ved chlorering med thionylchlorid i nærværelse af en katalysator DK176046B1 (da)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
ITMI951004		1995-05-18
ITMI951004A IT1275429B (it)	1995-05-18	1995-05-18	Processo per la preparazione di un intermedio utile nella sintesi di composti organici
PCT/EP1996/002009 WO1996036590A1 (fr)	1995-05-18	1996-05-10	Procede de preparation de dichlorure d'acide 5-amino-2,4,6-triiodo-isophtalique par chloration a l'aide de chlorure de thionyle en presence d'un catalyseur
EP9602009		1996-05-10

Publications (2)

Publication Number	Publication Date
DK130397A DK130397A (da)	1997-11-17
DK176046B1 true DK176046B1 (da)	2006-02-20

Family

ID=11371619

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK199701303A DK176046B1 (da)	1995-05-18	1996-05-10	Fremgangsmåde til fremstilling af 5-amino-2,4,6-triiodisophthalsyre-dichlorid ved chlorering med thionylchlorid i nærværelse af en katalysator

Country Status (20)

Country	Link
US (1)	US5663432A (fr)
JP (1)	JP3865405B2 (fr)
AU (1)	AU5895096A (fr)
BE (1)	BE1009466A3 (fr)
CA (1)	CA2221278C (fr)
CH (1)	CH691534A5 (fr)
CZ (1)	CZ287815B6 (fr)
DE (1)	DE19681399B4 (fr)
DK (1)	DK176046B1 (fr)
FR (1)	FR2734262B1 (fr)
GB (1)	GB2315751B (fr)
HU (1)	HUP9801142A3 (fr)
IE (1)	IE80674B1 (fr)
IL (1)	IL118062A (fr)
IT (1)	IT1275429B (fr)
NL (1)	NL1003127C2 (fr)
NO (1)	NO310286B1 (fr)
SE (1)	SE520616C2 (fr)
WO (1)	WO1996036590A1 (fr)
ZA (1)	ZA963788B (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN101307010B (zh) *	2008-07-12	2011-05-25	厦门大学	碘佛醇的合成方法
PT105770B (pt) *	2011-06-24	2013-07-08	Hovione Farmaciencia S A	Novo intermediário e seu uso na preparação de agente de contrate triiodado
PL2931696T3 (pl)	2012-12-11	2019-01-31	Bracco Imaging S.P.A	Ciągły sposób otrzymywania kwasu (S)-2-acetyloksypropionowego
HUE049284T2 (hu)	2014-06-10	2020-09-28	Bracco Imaging Spa	Eljárás (S)-2-acetiloxipropionsav és származékai elõállítására
WO2017056501A1 (fr) *	2015-10-02	2017-04-06	日本ゼオン株式会社	Procédé de production de solution d'halogénure d'acide, solution mixte et procédé de production d'un composé monoester
WO2017130871A1 (fr)	2016-01-26	2017-08-03	日本ゼオン株式会社	Procédé de production de solution d'halogénure d'acide et procédé de production de composé monoester
US10342232B1 (en)	2018-10-24	2019-07-09	The United States Of America As Represented By The Secretary Of The Navy	Iodinated polymers for biological agent defeat

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR825418A (fr) *	1936-08-10	1938-03-03	Bosch Robert	Pompe à combustibles liquides
US3655752A (en) *	1969-06-20	1972-04-11	Sterling Drug Inc	Isomers of 2 4 6-trihalo-n n n' n'-tetraalkylisophthalamides
CH608189A5 (fr) *	1974-12-13	1978-12-29	Savac Ag
GB1548594A (en) *	1976-06-11	1979-07-18	Nyegaard & Co As	Triiodoisophthalic acid amides
IT1193211B (it) *	1979-08-09	1988-06-15	Bracco Ind Chimica Spa	Derivati dell'acido 2,4,6-triiodo-isoftalico,metodo per la loro preparazione e mezzi di contrasto che li contengono
US4396598A (en) *	1982-01-11	1983-08-02	Mallinckrodt, Inc.	Triiodoisophthalamide X-ray contrast agent
FR2541676A1 (fr) *	1983-02-25	1984-08-31	Guerbet Sa	Composes non-ioniques a structures benzenique iodee ou bromee et produits opacifiants en contenant
US5075502A (en) *	1989-12-13	1991-12-24	Mallinckrodt, Inc.	Nonionic x-ray contrast agents, compositions and methods
AU3273993A (en) *	1991-12-03	1993-06-28	Mallinckrodt Medical, Inc.	Nonionic x-ray contrast agents, compositions and methods
IT1271107B (it) *	1994-11-29	1997-05-26	Zambon Spa	Processo per la preparazione di un intermedio utile nella sintesi di composti organici

1995
- 1995-05-18 IT ITMI951004A patent/IT1275429B/it active IP Right Grant
1996
- 1996-04-29 IL IL11806296A patent/IL118062A/xx not_active IP Right Cessation
- 1996-05-09 FR FR9605773A patent/FR2734262B1/fr not_active Expired - Lifetime
- 1996-05-10 CH CH02665/97A patent/CH691534A5/de not_active IP Right Cessation
- 1996-05-10 AU AU58950/96A patent/AU5895096A/en not_active Abandoned
- 1996-05-10 CZ CZ19973633A patent/CZ287815B6/cs not_active IP Right Cessation
- 1996-05-10 HU HU9801142A patent/HUP9801142A3/hu unknown
- 1996-05-10 DE DE19681399T patent/DE19681399B4/de not_active Expired - Lifetime
- 1996-05-10 WO PCT/EP1996/002009 patent/WO1996036590A1/fr not_active Ceased
- 1996-05-10 DK DK199701303A patent/DK176046B1/da not_active IP Right Cessation
- 1996-05-10 CA CA002221278A patent/CA2221278C/fr not_active Expired - Lifetime
- 1996-05-10 JP JP53453196A patent/JP3865405B2/ja not_active Expired - Lifetime
- 1996-05-10 GB GB9724181A patent/GB2315751B/en not_active Expired - Lifetime
- 1996-05-13 ZA ZA963788A patent/ZA963788B/xx unknown
- 1996-05-15 NL NL1003127A patent/NL1003127C2/nl not_active IP Right Cessation
- 1996-05-17 IE IE960350A patent/IE80674B1/en not_active IP Right Cessation
- 1996-05-17 US US08/649,490 patent/US5663432A/en not_active Expired - Lifetime
- 1996-05-20 BE BE9600446A patent/BE1009466A3/fr not_active IP Right Cessation
1997
- 1997-11-17 SE SE9704190A patent/SE520616C2/sv unknown
- 1997-11-17 NO NO19975260A patent/NO310286B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
WO1996036590A1 (fr)	1996-11-21
AU5895096A (en)	1996-11-29
IL118062A0 (en)	1996-08-04
ITMI951004A0 (it)	1995-05-18
IE960350A1 (en)	1996-11-27
ZA963788B (en)	1996-09-05
SE9704190D0 (sv)	1997-11-17
FR2734262A1 (fr)	1996-11-22
DE19681399T1 (de)	1998-05-20
IL118062A (en)	2001-03-19
US5663432A (en)	1997-09-02
ITMI951004A1 (it)	1996-11-18
SE520616C2 (sv)	2003-07-29
CA2221278C (fr)	2008-12-02
HUP9801142A1 (hu)	1998-08-28
NL1003127A1 (nl)	1996-11-19
GB9724181D0 (en)	1998-01-14
DK130397A (da)	1997-11-17
CH691534A5 (de)	2001-08-15
GB2315751B (en)	1999-04-14
SE9704190L (sv)	1997-11-17
NO975260L (no)	1997-11-17
CA2221278A1 (fr)	1996-11-21
HUP9801142A3 (en)	1998-09-28
FR2734262B1 (fr)	1997-08-29
NO975260D0 (no)	1997-11-17
NO310286B1 (no)	2001-06-18
DE19681399B4 (de)	2008-08-28
CZ363397A3 (cs)	1998-04-15
IE80674B1 (en)	1998-11-18
GB2315751A (en)	1998-02-11
IT1275429B (it)	1997-08-07
JPH11505234A (ja)	1999-05-18
NL1003127C2 (nl)	1999-08-25
BE1009466A3 (fr)	1997-04-01
CZ287815B6 (en)	2001-02-14
JP3865405B2 (ja)	2007-01-10

Publication	Publication Date	Title
DK176046B1 (da)	2006-02-20	Fremgangsmåde til fremstilling af 5-amino-2,4,6-triiodisophthalsyre-dichlorid ved chlorering med thionylchlorid i nærværelse af en katalysator
CN108503564A (zh)	2018-09-07	一种米库氯铵中间体及利用该中间体合成米库氯铵的方法
JPH0621089B2 (ja)	1994-03-23	芳香族エ−テルまたはチオエ−テル化合物の製造方法
US5856570A (en)	1999-01-05	Process for preparing 5-amino-2,4,6-triiodoisophthalic acid dichloride by chlorination of the corresponding acid in the presence of a tertiary amine salt or quaternary ammonium salt
US4496736A (en)	1985-01-29	Process for the preparation of carboxylic acids and N-tert.-alkylamines
KR0142667B1 (ko)	1998-07-15	티오펜-2,5-디카르복실산 디에스테르, 테트라하이드로 티오펜-2,5-디카르복실산 디에스테르 및 디벤족사졸릴 티오펜의 제조방법
US5744638A (en)	1998-04-28	Process for the preparation of haloanthranilic acids
JP2652563B2 (ja)	1997-09-10	芳香族ニトリル類の製造方法
WO2005014531A1 (fr)	2005-02-17	Procede de production de n-methacryloyl-4-cyano-3-trifluoromethylaniline, procede de stabilisation de ce compose, et procede de production de bicalutamide
US4267356A (en)	1981-05-12	Process for the preparation of N-(1'-alkoxycarbonylethyl)-2,6-dialkylanilines
JPH06166683A (ja)	1994-06-14	Ｏ，ｏ´−ジアシル酒石酸無水物の製造法
JP3640319B2 (ja)	2005-04-20	ベンズアミド誘導体の製造方法
KR102570646B1 (ko)	2023-08-23	트랜스-4-[4-(3-메톡시-4-니트로페닐)-1-피페라지닐]아다만탄-1-올 합성방법
US3960948A (en)	1976-06-01	Substituted chloroacylanilides
JP2773627B2 (ja)	1998-07-09	Ｏ，ｏ´−ジアシル酒石酸無水物の製造法
NL7904774A (nl)	1980-01-07	Werkwijze voor het bereiden van n,n'-di-gesubstiueerde 2-naftaleenethaanimidamiden.
KR0125930B1 (ko)	1997-12-26	테트라히드로프탈이미드 화합물의 제조방법
JPH0791246B2 (ja)	1995-10-04	ジメチルホルムアミドの精製法
JPH0853400A (ja)	1996-02-27	ヒドロキシカルボキシアニリドの製造方法
JPH027304B2 (fr)	1990-02-16
RU2000295C1 (ru)	1993-09-07	Способ получени полибромированных вторичных ароматических аминов
JPH01299245A (ja)	1989-12-04	スクアリン酸の製造方法
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