GB1285390A - Improvements in the n-alkylation of acylated amino compounds - Google Patents

Improvements in the n-alkylation of acylated amino compounds

Info

Publication number
GB1285390A
GB1285390A GB6045370A GB6045370A GB1285390A GB 1285390 A GB1285390 A GB 1285390A GB 6045370 A GB6045370 A GB 6045370A GB 6045370 A GB6045370 A GB 6045370A GB 1285390 A GB1285390 A GB 1285390A
Authority
GB
United Kingdom
Prior art keywords
alkylation
compounds
sulphate
dmso
reacted
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
Application number
GB6045370A
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.)
Pfizer Health AB
Original Assignee
Pharmacia AB
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.)
Filing date
Publication date
Application filed by Pharmacia AB filed Critical Pharmacia AB
Publication of GB1285390A publication Critical patent/GB1285390A/en
Expired legal-status Critical Current

Links

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
    • C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
    • C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
    • C07C209/18—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1285390 N-alkylation of acylated amino compounds PHARMACIA AB 21 Dec 1970 [23 Dec 1969] 60453/70 Heading C2C N-alkylation of acylated amino compounds is effected by reacting R.NH.acyl with an alkylating agent X.alkyl (wherein X is a reactive group or atom which can be split off during the alkylation process) in the presence of one or more compounds of the Formula (IV) (wherein R 3 and R 4 each is 1-5C alkyl, R 3 and R 4 together with the sulphur atom denote a saturated heterocyclic ring system) under alkaline conditions, and the product of formula optionally is deacylated to a secondary amine (where R<SP>1</SP> is the same as R or is an alkylated R). Compounds of Formula IV include dimethyl sulphoxide methylethyl sulphoxide, diethyl sulphoxide and sulpholane. The alkylating agent may be dimethyl sulphate or diethyl sulphate. In examples, (1) acetanilide in DMSO is methylated with dimethyl sulphate and N-methylacetanilide is recovered or the mixture is heated to yield N-methylaniline; (2) 3 - acetylamino - 5 - nitrobenzoic acid with similar reactants yields 3-methylamino-5-nitrobenzoic acid; (3) N-benzylacetamide yields N- methyl-N-benzylacetamide; (4) or using diethyl sulphate, N - ethyl - N - benzyl - acetamide is obtained; (5) 5-(3-acetamidopropylidene-10,11- dihydro - 5H - dibenzocycloheptane in DMSO with dimethylsulphate and KOH gives 5-(N- methyl - 3 - acetamidopropylidene) - 10,11- dihydro - 5H - dibenzocycloheptane which may be deacylated; (7) 2-amino-5-chlorobenzophenone is reacted with formic acid to yield 2<SP>1</SP>- benzoyl - 4<SP>1</SP> - chloroformanilide which is methylated and on standing forms 5-chloro-2- methylamino benzophenone; (8) 2-amino-5- chlorobenzophenone reacts with benzoyl chloride to form 2<SP>1</SP>-benzoyl-4<SP>1</SP>-chlorobenzanilide which is dissolved in DMSO with addition of KOH, reacted the dimethyl sulphate then heated to form 5-chloro-2-methylaminobenzo-phenone; in analogous manner 2-aminobenzophenones substituted in 5 position by Br, F, CF 3 , NO 2 or CH 3 O are reacted to form appropriate methylamino benzophenones.
GB6045370A 1969-12-23 1970-12-21 Improvements in the n-alkylation of acylated amino compounds Expired GB1285390A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
SE1785969 1969-12-23

Publications (1)

Publication Number Publication Date
GB1285390A true GB1285390A (en) 1972-08-16

Family

ID=20304064

Family Applications (1)

Application Number Title Priority Date Filing Date
GB6045370A Expired GB1285390A (en) 1969-12-23 1970-12-21 Improvements in the n-alkylation of acylated amino compounds

Country Status (5)

Country Link
CH (1) CH520108A (en)
DE (1) DE2063017A1 (en)
FR (1) FR2081393B1 (en)
GB (1) GB1285390A (en)
NL (1) NL7018733A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPWO2012029672A1 (en) * 2010-08-31 2013-10-28 Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 Pest control agent

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2436774A1 (en) * 1978-09-20 1980-04-18 Fabre Sa Pierre N-Alkylamino-benzophenone preparation - by reacting amino-benzophenone with alkylation agent, base, quat. ammonium catalyst etc. to give pharmaceutical intermediate (J5 28.3.80)
FR2436776A1 (en) * 1978-09-25 1980-04-18 Fabre Sa Pierre NOVEL ORTHO CHLORO BENZOYL-2 CHLORO-4 GLYCYLANILIDE DERIVATIVES, THEIR PREPARATION AND THEIR APPLICATION AS MEDICAMENTS
DE2919755A1 (en) 1979-05-16 1980-11-27 Hoechst Ag METHOD FOR PRODUCING N-VINYL-N-ALKYL-CARBONIC ACID AMIDES
DE2944456C2 (en) * 1979-11-03 1982-04-01 Hoechst Ag, 6000 Frankfurt Process for the preparation of N-? -Alkoxyalkyl-carboxamides
GB2092136B (en) * 1981-01-17 1985-06-05 Mitsui Toatsu Chemicals Production of n-substituted amide compounds

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPWO2012029672A1 (en) * 2010-08-31 2013-10-28 Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 Pest control agent
US9328068B2 (en) 2010-08-31 2016-05-03 Meiji Seika Pharma Co., Ltd. N-[1-((6-chloropyridin-3-yl) methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide for control of animal parasitic pests and agricultural/horticultural pests
US9717242B2 (en) 2010-08-31 2017-08-01 Meiji Seika Pharma Co., Ltd. N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide for control of agricultural/horticultural pests
US10085449B2 (en) 2010-08-31 2018-10-02 Meiji Seika Pharma Co., Ltd. N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2- trifluoroacetamide for control of agricultural/horticultural pests

Also Published As

Publication number Publication date
FR2081393A1 (en) 1971-12-03
NL7018733A (en) 1971-06-25
CH520108A (en) 1972-03-15
DE2063017A1 (en) 1972-10-05
FR2081393B1 (en) 1974-08-23

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee