GB783828A - Halogenated alkanamides and their preparation - Google Patents

Halogenated alkanamides and their preparation

Info

Publication number
GB783828A
GB783828A GB34138/55A GB3413855A GB783828A GB 783828 A GB783828 A GB 783828A GB 34138/55 A GB34138/55 A GB 34138/55A GB 3413855 A GB3413855 A GB 3413855A GB 783828 A GB783828 A GB 783828A
Authority
GB
United Kingdom
Prior art keywords
carbamylethyl
trichloroacetamide
ethyl
dichloroacetamide
formula
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
GB34138/55A
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.)
STWB Inc
Original Assignee
Sterling 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 Sterling Drug Inc filed Critical Sterling Drug Inc
Publication of GB783828A publication Critical patent/GB783828A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups

Landscapes

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

Abstract

The invention comprises compounds having the formula: <FORM:0783828/IV (a)/1> wherein Ar represents a phenyl, naphthyl, biphenyl, furyl, pyridyl or thienyl radical, X is a lower alkylene radical having one to four carbon atoms, Y is a lower a ,b -alkylene radical having two to four carbon atoms, R represents hydrogen or a hydrocarbon radical having from one to eight carbon atoms and Ac is a halogenated-(lower alkanoyl) radical having from two to four carbon atoms, compounds having the formula: <FORM:0783828/IV (a)/2> in which Z is halo or lower alkoxy and m is an integer from 1 to 3 inclusive and a process for the preparation of a compound having the formula I, which comprises reacting a compound having the formula: Ar-X-NH-Y-CONH-R with an acylating agent having the formula Ac-halogen or (Ac)2O, e.g. dichloroacetyl hloride or trichloroacetyl chloride. Examples describe the production of compounds having the formula: <FORM:0783828/IV (a)/3> whereinQ represents 2,4-di-Cl, H, 4-CH3, 4-OC4H4-n, 4-CH(CH3)2, 3,4-di-OCH3, 4-Cl, and 4 - N(CH3)2, N - phenylethyl - N - (2 - carbamylethyl - dichloracetamide, N - (1 - naphthylmethyl) - N - (2 - carbamylethyl) - dichloracetamide, N - (1 - biphenylmethyl) - N - (2-carbamylethyl) - dichloracetamide, N - (4 - n - hexylbenzyl) - N - (2 - carbamylethyl) - dibromoacetamide, N - (2,4 - diiodobenzyl) - N - (2-carbamylethyl) - bromochloroacetamide, N-(4 - nitrophenathyl) - N - (2 - carbamylethyl)-diiodoacetamide, N - [1 - (3,4,5 - triethoxyphenyl)ethyl] - N - (2 - carbamylpropyl)dichloroacetamide, N - [4 - (2,4 - dichlorophenyl) butyl] - N - (2 - carbamylpropyl) - 2,2 - dichloropropanamide, N - (4 - di - n - butylaminobenzyl) - N - (2 - carbamylbutyl) - 2,2 - diiodopropanamide, N - (4 - n - hexyloxybenzyl) - N-(2 - carbamylethyl) - 2 - bromo - 3 - chloropropanamide, N - (4 - n - butyl - mercaptobenzyl)-N - (2 - carbamylethyl) - 2,2,3 - trichloropropanamide, N - (4 - n - butylsulphonylbenzyl) - N-(2 - carbamylethyl) - 2,2 - dichlorobutanamide, N - (2,4 - dichlorobenzyl) - N - (2 - carbamylethyl) - 3,4 - dibromobutanamide, N - (4 - n-butoxybenzyl) - N - (2 - carbamylethyl) - 2,2,3-trichlorobutanamide, N - (4 - chlorobenzyl)-N - (2 - carbamylethyl) - 2,3,4 - trichlorobutamide, N - (2 - furylmethyl) - N - (2 - carbamylethyl) - dichloroacetamide, N - (2 - thienylmethyl) - N - (2 - carbamylethyl) - dichloroacetamide, N - (2 - pyridylmethyl) - N - (2-carbamylethyl) - dichloroacetamide, N - (3-pyridylmethyl) - N - (2 - carbamylethyl) - dichloroacetamide, N - (5 - chloro - 2 - pyridylmethyl) - N - (2 - carbamylpropyl) - dichloroacetamides, N - (4 - n - butoxybenzyl) - N - (2-carbamylethyl) - trichloroacetamide, N - (4-chlorobenzyl) - N - (2 - carbamylethyl) - trichloroacetamide, N - benzyl - N - (2 - carbamylethyl) - trichloroacetamide, N - phenylethyl-N - (2 - carbamylethyl) - trichloroacetamide, N - (2,4 - dichlorobenzyl) - N - (2 - carbamylethyl) - trichloroacetamide, N - (4 - isopropylbenzyl) - N - (2 - carbamylethyl) - trichloroacetamide, N - (3,4,5 - triiodobenzyl) - N - (2-carbamylethyl) - trichloroacetamide, N - (2,4-dichlorophenethyl) - N - (2 - carbamylethyl)-trichloroacetamide, N - (4 - isobutylbenzyl)-N - (2 - carbamylbutyl) - trichloroacetamide, N - (3,4 - dibromobenzyl) - N - (2 - carbamylpropyl) - tribromoacetamide, N - (4 - chlorobenzyl) - N - (2 - carbamylethyl) - chloracetamide, N - (2,4 - dichlorobenzyl) - N - (2 - carbamylethyl) - chloracetamide, N - (3,4 - dimethoxybenzyl) - N - (2 - carbamylethyl) - 3 - chloropropanamide, N - (4 - n - butoxybenzyl)-N - (2 - carbamylethyl) - 4 - bromobutanamide, N - (3,4 - dibromobenzyl) - N - (2 - carbamylethyl) - bromoacetamide, N - (4 - n - hexylbenzyl) - N - (2 - carbamylbutyl) - fluoroacetamide, N - (2,4 - diiodobenzyl) - N - (2 - carbamylpropyl) - iodoacetamide, N - (2,4 - dichlorophenethyl) - N - (2 - carbamylethyl) - chloracetamide, N - (4 - isopropylbenzyl) - N - [2-(ethylcarbamyl)ethyl]dichloroacetamide, N-[4 - isopropylbenzyl) - N - [2 - (n - hexylcarbamyl)ethyl]dibromoacetamide, N - (2,4 - dichlorobenzyl) - N - [2 - allylcarbamyl)ethyl]-trichloroacetamide, N - (4 - n - butoxybenzyl)-N - [2 - (cyclopentylcarbamyl)propyl]iodoacetamide, N - (3,4 - dibromobenzyl) - N - [2 - cyclohexylmethylcarbamyl)ethyl] - 2,2 - dichloroprepanamide, N - (4 - chlorobenzyl) - N - [2-(phenylcarbamyl)butyl] - 2,3 - dichloropropanamide, N - [2 - (3,4 - diethoxyphenyl)ethyl]-N - [2 - (3-ethylphenylcarbamyl)ethyl] - 2,3,4-trichlorobutanamide, N - (2,4 - dichlorobenzyl)-N - [2 - (benzylcarbamyl)ethyl] - 2,2 - dibromobutanamide and N - (4 - nitrobenzyl) - N - [2-(phenethylcarbamyl) ethyl] dichloroacetamide. The intermediate compounds Ar-X-NH-Y-CONH2 are obtained by reacting an aralkylamine Ar-X-NH2 with a 2-alkenamide, e.g. N - (2 - carbamylethyl) - 2,4 - dichlorobenzylamine is obtained by reacting 2,4-dichlorobenzene with acrylamide.
GB34138/55A 1954-12-27 1955-11-29 Halogenated alkanamides and their preparation Expired GB783828A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US783828XA 1954-12-27 1954-12-27

Publications (1)

Publication Number Publication Date
GB783828A true GB783828A (en) 1957-10-02

Family

ID=22143694

Family Applications (1)

Application Number Title Priority Date Filing Date
GB34138/55A Expired GB783828A (en) 1954-12-27 1955-11-29 Halogenated alkanamides and their preparation

Country Status (1)

Country Link
GB (1) GB783828A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN117603082A (en) * 2024-01-22 2024-02-27 深圳智微通科技有限公司 Method for continuously synthesizing N-butyl-2-chloroacetamide by utilizing microchannel reaction device

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN117603082A (en) * 2024-01-22 2024-02-27 深圳智微通科技有限公司 Method for continuously synthesizing N-butyl-2-chloroacetamide by utilizing microchannel reaction device
CN117603082B (en) * 2024-01-22 2024-03-19 深圳智微通科技有限公司 Method for continuously synthesizing N-butyl-2-chloroacetamide by utilizing microchannel reaction device

Similar Documents

Publication Publication Date Title
GB1468283A (en) N-1-omega-phenylalkyl-piperidyl-4-n-alpha-pyridyl-carbonic acid amides
GB783828A (en) Halogenated alkanamides and their preparation
GB1094205A (en) Process for the preparation of amino-acid surface active agents
GB1077180A (en) Novel n-(thiocarbamoylthio)-imides
GB964712A (en) Acetamide derivatives
GB966818A (en) 2-halo-3-mercapto-quinoxaline substitution products and process for their production
GB862974A (en) Curing compounds for epoxy resins
GB1016240A (en) Guanidine derivatives and a process for the manufacture thereof
US2249135A (en) Beta, beta&#39;-dicyanodiethyl cyanamide
GB1352288A (en) Imidazole derivatives
GB699858A (en) Improvements in the production of photographic images
GB1056313A (en) Coccidiostatic compositions
GB1118798A (en) Substituted benzylamines
GB1109308A (en) Heterocyclic alkanoic acid amides
GB1158250A (en) Imidazoline Derivatives
GB1044933A (en) Improved method for the preparation of 1-(1-phenyl-ethyl)-5-[(r) (ar) n-co]-imidazoles and compounds produced thereby
GB844946A (en) New 2-(n-substituted)-acylamino-1,3,4-thiadiazole-5-sulfonamides
GB1124261A (en) Naphthofuran derivatives
GB741228A (en) Improvements in or relating to triazole compounds
GB1185080A (en) Pyrrolidines
GB696473A (en) Improvements in and relating to the manufacture of heterocyclic compounds
GB706162A (en) Substituted benzamides and fungicidal compositions containing same
GB1173833A (en) N-Aminoalkyl-N-Benzylamides
ES279237A1 (en) N-substituted derivatives of 2-amino-1-(2,5-dimethoxy-phenyl)propan-1-ol
GB701554A (en) Improvements relating to new di-substituted piperazines