JPS6312467B2 - - Google Patents

Info

Publication number: JPS6312467B2
Authority: JP; Japan
Prior art keywords: isovaleric acid; bromoisovaleric; urea; acid; added
Prior art date: 1981-03-13
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

Application number

JP3713481A

Other languages

English (en)

Japanese (ja)

Other versions

JPS57150653A (en

Inventor

Masao Kawamura

Masayoshi Takemoto

Haruichiro Maeda

Seiichi Akutsu

Yukio Kono

Masahide Takahashi

Hirotsugu Konishi

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sumitomo Seika Chemicals Co Ltd

Original Assignee

Seitetsu Kagaku Co Ltd

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.)

1981-03-13

Filing date

1981-03-13

Publication date

1988-03-18

1981-03-13 Application filed by Seitetsu Kagaku Co Ltd filed Critical Seitetsu Kagaku Co Ltd

1981-03-13 Priority to JP3713481A priority Critical patent/JPS57150653A/ja

1982-09-17 Publication of JPS57150653A publication Critical patent/JPS57150653A/ja

1988-03-18 Publication of JPS6312467B2 publication Critical patent/JPS6312467B2/ja

Status Granted legal-status Critical Current

Links

GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 claims description 29
GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 29
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 22
XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 claims description 21
-1 isovaleric acid halide Chemical class 0.000 claims description 20
238000006243 chemical reaction Methods 0.000 claims description 18
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
229910052794 bromium Inorganic materials 0.000 claims description 14
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 12
239000004202 carbamide Substances 0.000 claims description 12
238000000034 method Methods 0.000 claims description 11
CMCCHHWTTBEZNM-UHFFFAOYSA-N 2-bromo-N-carbamoyl-3-methylbutanamide Chemical compound CC(C)C(Br)C(=O)NC(N)=O CMCCHHWTTBEZNM-UHFFFAOYSA-N 0.000 claims description 9
239000002904 solvent Substances 0.000 claims description 6
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 5
MVYUMPZRKNBHOP-UHFFFAOYSA-N 2-bromo-3-methylbutanoyl chloride Chemical compound CC(C)C(Br)C(Cl)=O MVYUMPZRKNBHOP-UHFFFAOYSA-N 0.000 claims description 5
150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 4
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 3
239000007788 liquid Substances 0.000 claims description 3
239000003054 catalyst Substances 0.000 description 13
238000005893 bromination reaction Methods 0.000 description 7
239000002994 raw material Substances 0.000 description 7
UEBARDWJXBGYEJ-UHFFFAOYSA-N 2-bromo-3-methylbutanoic acid Chemical compound CC(C)C(Br)C(O)=O UEBARDWJXBGYEJ-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
235000014113 dietary fatty acids Nutrition 0.000 description 4
229930195729 fatty acid Natural products 0.000 description 4
239000000194 fatty acid Substances 0.000 description 4
229910052698 phosphorus Inorganic materials 0.000 description 4
239000011574 phosphorus Substances 0.000 description 4
CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
230000032683 aging Effects 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000003814 drug Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000203 mixture Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
229950011008 tetrachloroethylene Drugs 0.000 description 2
LBXKQIWKQYEXRO-UHFFFAOYSA-N 3-methylbutanoyl bromide Chemical compound CC(C)CC(Br)=O LBXKQIWKQYEXRO-UHFFFAOYSA-N 0.000 description 1
ISULZYQDGYXDFW-UHFFFAOYSA-N 3-methylbutanoyl chloride Chemical compound CC(C)CC(Cl)=O ISULZYQDGYXDFW-UHFFFAOYSA-N 0.000 description 1
244000025254 Cannabis sativa Species 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000012320 chlorinating reagent Substances 0.000 description 1
238000005660 chlorination reaction Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000005554 hypnotics and sedatives Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
BZRZRAJFBZQJRU-UHFFFAOYSA-N n-bromo-n-carbamoyl-3-methylbutanamide Chemical compound CC(C)CC(=O)N(Br)C(N)=O BZRZRAJFBZQJRU-UHFFFAOYSA-N 0.000 description 1
XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 1
150000003017 phosphorus Chemical class 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000001577 simple distillation Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000002699 waste material Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP3713481A 1981-03-13 1981-03-13 Preparation of alpha-bromoisovalerylurea Granted JPS57150653A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP3713481A JPS57150653A (en)	1981-03-13	1981-03-13	Preparation of alpha-bromoisovalerylurea

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP3713481A JPS57150653A (en)	1981-03-13	1981-03-13	Preparation of alpha-bromoisovalerylurea

Publications (2)

Publication Number	Publication Date
JPS57150653A JPS57150653A (en)	1982-09-17
JPS6312467B2 true JPS6312467B2 (de)	1988-03-18

Family

ID=12489139

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP3713481A Granted JPS57150653A (en)	1981-03-13	1981-03-13	Preparation of alpha-bromoisovalerylurea

Country Status (1)

Country	Link
JP (1)	JPS57150653A (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN100333913C (zh)	2002-07-08	2007-08-29	精工爱普生株式会社	喷液装置
CN108395387A (zh) *	2018-04-28	2018-08-14	苏州莱克施德药业有限公司	一种溴米索伐的合成方法
CN110204460A (zh) *	2019-06-04	2019-09-06	华润双鹤利民药业（济南）有限公司	一种溴米索伐制作工艺流程

1981
- 1981-03-13 JP JP3713481A patent/JPS57150653A/ja active Granted

Also Published As

Publication number	Publication date
JPS57150653A (en)	1982-09-17

Publication	Publication Date	Title
US4769493A (en)	1988-09-06	Process for producing tetrafluorophthalic acid
US4155940A (en)	1979-05-22	M-Bromo-benzotrifluorides
JPS6312467B2 (de)	1988-03-18
CA2090768A1 (en)	1993-08-27	Process for the preparation of 2,4,5-trifluorobenzonitrile
JPS63316753A (ja)	1988-12-26	７個より多い炭素原子を有するカルボン酸ハロゲニドの製法
US4191711A (en)	1980-03-04	Process for the preparation of certain nuclear chlorinated benzotrichlorides
JPS625899B2 (de)	1987-02-07
JPS635017B2 (de)	1988-02-01
KR100243453B1 (ko)	2000-02-01	메틸 방향족 화합물의 자유-라디칼 염소화 또는 브롬화 방법
JP2001187762A (ja)	2001-07-10	高純度芳香族酸クロライドの製造方法
US4093638A (en)	1978-06-06	Simultaneous preparation of organic acid chlorides and trichloroacryloyl chloride and product
EP0168732B1 (de)	1988-07-27	Verfahren zur Herstellung von halogenierten Aroylessigestern
JP4221782B2 (ja)	2009-02-12	ジハロトリフルオロアセトンの精製方法
JP3298346B2 (ja)	2002-07-02	高純度２−クロロテレフタル酸クロライドの製造方法
US5279719A (en)	1994-01-18	Method for chlorination of methylated aromatic compounds
US1930751A (en)	1933-10-17	Chlorination of omicron-toluidine
JPH041143A (ja)	1992-01-06	３，５―ジ―第三級ブチル―２，６―ジクロロトルエンの製造方法
JP4303685B2 (ja)	2009-07-29	２−シクロペンテン−１−オンの製造方法
JPS62175438A (ja)	1987-08-01	マロン酸誘導体の製造方法
JPS6314693B2 (de)	1988-04-01
JPS5935375B2 (ja)	1984-08-28	モノクロルカルボン酸クロライドの製造法
JPH11199544A (ja)	1999-07-27	２−ホルミル安息香酸核塩素化物類の製造法
JPH0148251B2 (de)	1989-10-18
JPH02101030A (ja)	1990-04-12	５−ブチル−２，３，６−トリクロロトルエンの製造方法
JPH08198805A (ja)	1996-08-06	アルキルベンゾイルクロライドの製造方法