CA1308732C - Methode de preparation de derives d'amines - Google Patents

Methode de preparation de derives d'amines

Info

Publication number: CA1308732C
Authority: CA; Canada
Prior art keywords: formula; compound; methyl; nitromethane; reaction
Prior art date: 1984-06-15
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 - Fee Related

Application number

CA000590391A

Other languages

English (en)

Inventor

John Frederick Seager

Roger Dansey

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.)

Glaxo Group Ltd

Original Assignee

Glaxo Group 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.)

1984-06-15

Filing date

1989-02-07

Publication date

1992-10-13

1984-06-15 Priority claimed from GB848415254A external-priority patent/GB8415254D0/en

1989-02-07 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

1992-10-13 Application granted granted Critical

1992-10-13 Publication of CA1308732C publication Critical patent/CA1308732C/fr

2009-10-13 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

238000002360 preparation method Methods 0.000 title claims abstract description 12
150000001412 amines Chemical class 0.000 title claims abstract description 8
150000001875 compounds Chemical class 0.000 claims abstract description 39
238000000034 method Methods 0.000 claims abstract description 22
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 3
238000006243 chemical reaction Methods 0.000 claims description 18
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 17
LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 claims description 16
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 12
239000002904 solvent Substances 0.000 claims description 12
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 11
229960001760 dimethyl sulfoxide Drugs 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000002168 alkylating agent Substances 0.000 claims description 6
229940100198 alkylating agent Drugs 0.000 claims description 6
150000001768 cations Chemical group 0.000 claims description 6
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 claims description 4
238000005804 alkylation reaction Methods 0.000 claims description 3
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical group COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 3
150000002431 hydrogen Chemical group 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
239000002253 acid Substances 0.000 claims description 2
150000001350 alkyl halides Chemical class 0.000 claims description 2
230000029936 alkylation Effects 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
229940102396 methyl bromide Drugs 0.000 claims description 2
230000002152 alkylating effect Effects 0.000 claims 1
150000003467 sulfuric acid derivatives Chemical class 0.000 claims 1
239000003485 histamine H2 receptor antagonist Substances 0.000 abstract description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
229910000104 sodium hydride Inorganic materials 0.000 description 8
239000012312 sodium hydride Substances 0.000 description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
239000000203 mixture Substances 0.000 description 7
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
239000002585 base Substances 0.000 description 6
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 6
238000011065 in-situ storage Methods 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 5
-1 isothiocyanate ester Chemical class 0.000 description 5
238000003756 stirring Methods 0.000 description 5
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
239000006184 cosolvent Substances 0.000 description 3
YQFHPXZGXNYYLD-UHFFFAOYSA-N n-methyl-1-methylsulfanyl-2-nitroethenamine Chemical compound CNC(SC)=C[N+]([O-])=O YQFHPXZGXNYYLD-UHFFFAOYSA-N 0.000 description 3
SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
SDIXRDNYIMOKSG-UHFFFAOYSA-L disodium methyl arsenate Chemical compound [Na+].[Na+].C[As]([O-])([O-])=O SDIXRDNYIMOKSG-UHFFFAOYSA-L 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
230000011987 methylation Effects 0.000 description 2
238000007069 methylation reaction Methods 0.000 description 2
QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
VMXUWOKSQNHOCA-LCYFTJDESA-N ranitidine Chemical compound [O-][N+](=O)/C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-LCYFTJDESA-N 0.000 description 2
229960000620 ranitidine Drugs 0.000 description 2
239000007858 starting material Substances 0.000 description 2
VQBVPDAUEBSGMB-UHFFFAOYSA-N 1-n,1-n'-dimethyl-2-nitroethene-1,1-diamine Chemical compound CNC(NC)=C[N+]([O-])=O VQBVPDAUEBSGMB-UHFFFAOYSA-N 0.000 description 1
244000025254 Cannabis sativa Species 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 1
239000012022 methylating agents‎ Substances 0.000 description 1
FBHJXWOURBPAKR-UHFFFAOYSA-N n-(1-methylsulfanyl-2-nitroethenyl)aniline Chemical compound [O-][N+](=O)C=C(SC)NC1=CC=CC=C1 FBHJXWOURBPAKR-UHFFFAOYSA-N 0.000 description 1
101150009274 nhr-1 gene Proteins 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
SGXXNSQHWDMGGP-IZZDOVSWSA-N nizatidine Chemical compound [O-][N+](=O)\C=C(/NC)NCCSCC1=CSC(CN(C)C)=N1 SGXXNSQHWDMGGP-IZZDOVSWSA-N 0.000 description 1
229960004872 nizatidine Drugs 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229940117953 phenylisothiocyanate Drugs 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000000725 suspension Substances 0.000 description 1

Landscapes

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

CA000590391A 1984-06-15 1989-02-07 Methode de preparation de derives d'amines Expired - Fee Related CA1308732C (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB848415254A GB8415254D0 (en)	1984-06-15	1984-06-15	Amine derivatives
GB8415254		1984-06-15
CA000484041A CA1256454A (fr)	1984-06-15	1985-06-14	Preparation de derives de l'amine

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000484041A Division CA1256454A (fr)	1984-06-15	1985-06-14	Preparation de derives de l'amine

Publications (1)

Publication Number	Publication Date
CA1308732C true CA1308732C (fr)	1992-10-13

Family

ID=25670713

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000590391A Expired - Fee Related CA1308732C (fr)	1984-06-15	1989-02-07	Methode de preparation de derives d'amines

Country Status (1)

Country	Link
CA (1)	CA1308732C (fr)

1989
- 1989-02-07 CA CA000590391A patent/CA1308732C/fr not_active Expired - Fee Related

Legal Events

Date	Code	Title	Description
2005-10-13	MKLA	Lapsed

Publication	Publication Date	Title
CA1308732C (fr)	1992-10-13	Methode de preparation de derives d'amines
WO2001036383A1 (fr)	2001-05-25	Procede de preparation de sulfamides
CA1256454A (fr)	1989-06-27	Preparation de derives de l'amine
CA1300629C (fr)	1992-05-12	Procede pour la production d'intermediaires amidine-acide sulfonique pour la synthese des guanidines
US4781866A (en)	1988-11-01	Process for producing amidine sulfonic acid intermediates for guanidines
KR100499901B1 (ko)	2006-04-12	피리딜메틸이소티오시아네이트의제조방법
SU677657A3 (ru)	1979-07-30	Способ получени -формилированных соединений
US3997605A (en)	1976-12-14	Preparation of formamide compounds
HUT58285A (en)	1992-02-28	Process for producing substituted ethylene derivatives
AU598714B2 (en)	1990-06-28	Process for preparing substituted guanylthioureas
WO1992015562A2 (fr)	1992-09-17	Preparation d'alcanamide omega-substitue
US6740768B1 (en)	2004-05-25	Method for producing symmetrical and asymmetrical carbonates
KR790001309B1 (ko)	1979-09-24	우라실 유도체의 제조법
EP0339964B1 (fr)	1994-12-14	Synthèse de 4-methyl-3-thiosemicarbazide
GB1570912A (en)	1980-07-09	Aromatic sulphonamido derivatives and process for their manufacture
FI90061B (fi)	1993-09-15	Foerfarande foer framstaellning av aminderivat
EP0699184B1 (fr)	1998-04-22	Preparation de n-cyanodithioiminocarbonates symetriques ou asymetriques a disubstitution
JP3569428B2 (ja)	2004-09-22	ホモアリルアミン類の製造方法
JPH0253764A (ja)	1990-02-22	ジチオビスフェノールの製造方法
WO1999044996A1 (fr)	1999-09-10	Procede relatif a l'elaboration d'acide 3-hydroxy-5-[1,4,5,6-tetrahydro-5-hydroxy-2-pyrimidinyle)amino]benzoique
JPS6343382B2 (fr)	1988-08-30
KR960005518B1 (ko)	1996-04-25	1-아미노-4-[[2-(치환된아미노)메틸-4-메틸-6-술포페닐]아미노]-9,10-디히드로-9, 10-디옥소-2-안트라센술폰산의 제조방법
KR960010101B1 (ko)	1996-07-25	4-오르소토릴티오세미카바지드의 제조방법
KR970074760A (ko)	1997-12-10	N-(2-아미노-3, 5-디브로모벤조일)-n-(알칸술포닐)하이드라지드의 제조방법
JPS58121285A (ja)	1983-07-19	ビスシクロヘプタトリエノ−テトラアザ−ジオキサ又はジチア−シクロアルケン