GB747592A - N-(substituted-benzyl)-n-(hydroxyalkyl or lower alkyl) dihaloacetamides and the preparation thereof - Google Patents

N-(substituted-benzyl)-n-(hydroxyalkyl or lower alkyl) dihaloacetamides and the preparation thereof

Info

Publication number
GB747592A
GB747592A GB35726/53A GB3572653A GB747592A GB 747592 A GB747592 A GB 747592A GB 35726/53 A GB35726/53 A GB 35726/53A GB 3572653 A GB3572653 A GB 3572653A GB 747592 A GB747592 A GB 747592A
Authority
GB
United Kingdom
Prior art keywords
dichlorobenzyl
isopropyl
hydroxyethyl
substituted
hydroxypropyl
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
GB35726/53A
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.)
STIRLING DRUG Inc
Original Assignee
STIRLING DRUG Inc
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 STIRLING DRUG Inc filed Critical STIRLING DRUG Inc
Publication of GB747592A publication Critical patent/GB747592A/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/18—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises N-substituted dihaloacetamides of the formula Ar-CH2-NR-CO-CH(Hal)2 where Ar is substituted phenyl, the substituents being one or more halogen, alkyl, alkoxy, methylenedioxy, ethylenedioxy, alkylthio, alkylsulphonyl or nitro groups, and R is alkyl, b -hydroxyalkyl or g -hydroxyalkyl having not more than 6 carbon atoms. The products are made by acylating the appropriate substituted benzylamines with dihaloacetyl halides or (when R is hydroxyalkyl) alkyl dihaloacetates. All the halogen atoms mentioned above can be chlorine, bromine, fluorine or iodine. Examples are given of the preparation of the following substituted dichloracetamides: N - (3:4 - dichlorobenzyl) - N - (2 - hydroxyethyl), N - (2:4-dichlorobenzyl) - N - (2 - hydroxyethyl), N - (p - chlorobenzyl) - N - (2 - hydroxyethyl), N - (p - ethoxybenzyl) - N - (2 - hydroxyethyl), N - (p - isopropylbenzyl) - N - (2 - hydroxyethyl), N - piperonyl - N - (2 - hydroxyethyl), N - (p - nitrobenzyl) - N - (2 - hydroxyethyl), N - (p - butoxybenzyl) - N - (2 - hydroxyethyl), N - (2:4 - dichlorobenzyl) - N - (2 - hydroxypropyl), N - (3:4 - dichlorobenzyl - N - (2 - hydroxypropyl), N - (o - chlorobenzyl) - N - (2 - hydroxyethyl), N - (3:4 - dichlorobenzyl) - N - (3 - hydroxy - propyl), N - (2:4 - dichlorobenzyl) - N - (3 - hydroxypropyl), N - (3:4 - dimethoxybenzyl) - N - (2 - hydroxyethyl), N - (2:4 - dichlorobenzyl) - N - isopropyl, N - (p - butoxybenzyl) - N - isopropyl, N - (p - isopropylbenzyl) - N - isopropyl, N - (p - nitrobenzyl) - N - isopropyl, N - (2:3 - dimethoxybenzyl) - N - ethyl, N - (2:4 - dichlorobenzyl) - N - n - butyl, N - (2:4 - dichlorobenzyl) - N - sec. - butyl, N - (3:4 - dichlorobenzyl) - N - n - butyl, N - (2:4 - dichlorobenzyl) - N - n - propyl, N - (3:4 - dichlorobenzyl) - N - isobutyl, N - (o - methoxybenzyl) - N - ethyl, N - (3:4 - dichlorobenzyl) - N - isopropyl, N - (p - chlorobenzyl) - N - isopropyl, N - piperonyl - N - isopropyl, N - (p - methylbenzyl) - N - isopropyl and N - (o - chlorobenzyl) - N - isopropyl. The preparation of N - (2:4 - dichlorobenzyl) - and N - (3:4 - dichlorobenzyl) - N - (2 - hydroxyethyl) - dibromacetamides is also described. Other products mentioned are N-(3:4:5-triethoxybenzyl) - N - (2 - hydroxypropyl) - dibromacetamide, N - (p - nitrobenzyl) - N - (2 - hydroxyethyl) - difluoracetamide, N - (3:4:5 - tribromobenzyl) - N - isopropyl - dichloracetamide, N - (3:4 - diethoxybenzyl) - N - isobutyl - dibromacetamide, N - (p - nitrobenzyl) - N - n hexyl - di - iodoacetamide, N - (2:4 - dichlorobenzyl) - N - isopropylbromochloracetamide, N - (p - n - butylthiobenzyl) - N - (2 - hydroxyethyl) - dichloroacetamide, N - (p - n - butylthiobenzyl) - N - isopropyl - dichloracetamide, N-(p-isobutylsulphonylbenzyl)-N-(2-hydroxyethyl) - dichloracetamide and N - (p - n - butylsulphonylbenzyl) - N - isopropyl - dichloracetamide. Various other alkyl, alkoxy, alkylthio and alkylsulphonyl groups are mentioned as substituents in Ar and various alkyl and hydroxyalkyl groups for R. Substituted benzylamines Ar-CH2-NH-R are made by reacting R-NH2 with a nuclearsubstituted benzyl halide or by catalytically reducing the reaction product of R-NH2 with a substituted benzylamine (probably a Schiff's base). Examples are given of the production of 2 - (p - isopropylbenzylamino) - ethanol, 2 - (p - methoxybenzylamino) - ethanol, 2 - (2:4-dichlorobenzylamino) - ethanol, N - isopropyl - 2:4 - dichlorobenzylamine and N - isopropyl - 4 - n - butoxybenzylamine. Other products are mentioned in which R is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec.butyl, 2-hydroxyethyl and 2-hydroxypropyl, and the nuclear substituents are methyl, isopropyl, methoxy, dimethoxy, ethoxy, methylenedioxy, butoxy, chloro, dichloro, tribromo, tri-iodo and nitro.
GB35726/53A 1953-01-02 1953-12-23 N-(substituted-benzyl)-n-(hydroxyalkyl or lower alkyl) dihaloacetamides and the preparation thereof Expired GB747592A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US747592XA 1953-01-02 1953-01-02

Publications (1)

Publication Number Publication Date
GB747592A true GB747592A (en) 1956-04-11

Family

ID=22121532

Family Applications (1)

Application Number Title Priority Date Filing Date
GB35726/53A Expired GB747592A (en) 1953-01-02 1953-12-23 N-(substituted-benzyl)-n-(hydroxyalkyl or lower alkyl) dihaloacetamides and the preparation thereof

Country Status (1)

Country Link
GB (1) GB747592A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3143566A (en) * 1959-10-08 1964-08-04 Sterling Drug Inc Nu, nu'-di-[halogenated-(lower-alkanoyl)]-diamine compositions and their preparation
EP0190105A2 (en) * 1985-01-31 1986-08-06 Ciba-Geigy Ag Herbicidal agent
US4897109A (en) * 1984-05-28 1990-01-30 Ciba-Geigy Corporation Compositions for protecting culture plants from the phytotoxic action of herbicidally active chloracetanilides

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3143566A (en) * 1959-10-08 1964-08-04 Sterling Drug Inc Nu, nu'-di-[halogenated-(lower-alkanoyl)]-diamine compositions and their preparation
US4897109A (en) * 1984-05-28 1990-01-30 Ciba-Geigy Corporation Compositions for protecting culture plants from the phytotoxic action of herbicidally active chloracetanilides
EP0190105A2 (en) * 1985-01-31 1986-08-06 Ciba-Geigy Ag Herbicidal agent
EP0190105A3 (en) * 1985-01-31 1988-10-26 Ciba-Geigy Ag Herbicidal agent

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