GB767148A - New acetanilide derivatives and the manufacture thereof - Google Patents
New acetanilide derivatives and the manufacture thereofInfo
- Publication number
- GB767148A GB767148A GB21458/54A GB2145854A GB767148A GB 767148 A GB767148 A GB 767148A GB 21458/54 A GB21458/54 A GB 21458/54A GB 2145854 A GB2145854 A GB 2145854A GB 767148 A GB767148 A GB 767148A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- hydroxy
- methoxy
- dichloracet
- methylanilide
- 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
Links
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises compounds of the formula <FORM:0767148/IV(b)/1> in which R is an alkyl or aralkyl radical, and in which the phenyl radical X is substituted by one or more groups (which may be the same or different) selected from nitro, hydroxy, alkoxy, aralkoxy, aryloxy, carboxyalkoxy, alkenoxy, alkylenedioxy, and -NR1R2 groups wherein R1 and R2 may be the same or different and represent hydrogen, or alkyl groups; also a process for their preparation by reacting the corresponding N-alkyl or aralkylamino compound (except those substituted by primary or secondary amino groups) with dichloracetyl chloride in the presence of an acid-binding agent, which may be sodium acetate or an excess of the amine reactant. The compounds wherein X contains one or more nitrogroups may also be produced by direct nitration and the corresponding primary amino compounds then obtained by reduction, preferably with stannous chloride. The alkoxy and aralkoxy compounds may be prepared from the corresponding hydroxy compounds by alkylation or aralkylation. In examples: dichloroacetyl chloride in benzene is added slowly to a cooled mixture of p-methylaminophenol sulphate, sodium bisulphite and sodium acetate trihydrate in benzene, when dichloroacet-4-hydroxy-N-methylanilide separates; other dichloracetanilides similarly prepared are 2-hydroxy - N - methyl-, 2 - hydroxy - N - ethyl-, 3 - hydroxy - N - methyl-, 4 - hydroxy - N - ethyl-, 4 - butoxy - N - methyl-, 4 - methoxy - N - methyl-, 4 - methoxy - N - ethyl-, 4-ethoxy-N - methyl-, 4 - hydroxy - N - propyl-, 4 - hydroxy - N - benzyl-, 3 - methoxy - N - methyl-, 4 - methoxy - N - propyl-, 4 - n - propoxy - N - methyl-, 4 - isopropoxy - N - methyl-, 4 - allyl - oxy - N - methyl-, 4 - phenoxy - N - methyl-, 2-methoxy - N - methyl-, 3,4 - dimethoxy - N - methyl-, 2 - n - butoxy - N - methyl-, 3 - nitro-N - methyl-, 4 - nitro - N - methyl-, and 4-dimethylamino - N - methyl- and using methyl propyl ketone as solvent 3,4-dihydroxy-N-methyl-, and 3,5 - dihydroxy - N - ethyl-. Phloroglucinol and aqueous methylamine are reacted in the absence of air, and then treated with dichloroacetyl chloride in methyl propyl ketone, giving dichloracet-3,5-dihydroxy-N-methylanilide; dichloracet - 4 - methoxy - N - methyl-, 4 - butoxy - N - methyl-, 3 - butoxy-N - methyl- and 4 - benzyloxy - N - methyl-anilides and 4-(dichloro - N - methylacetamido)-phenoxyacetic acid are prepared from the corresponding hydroxy compounds by etherification using potassium carbonate and the appropriate alkyl or aralkyl halide or ethyl bromoacetate. 4-Methylaminoveratrole, acetic acid and aqueous HBr are refluxed together, the solvent distilled off and the residue treated with dichloracetyl chloride and sodium acetate in aqueous benzene, giving dichloracet-3-hydroxy-4 -methoxy-N-methylanilide; 4-nitromethylenedioxybenzene is hydrogenated over palladium charcoal and the resulting 4-aminomethylenedioxy benzene formylated to give 3,4-methylenedioxyformanilide, which is N-methylated using methyl iodide, potassium hydroxide in acetone, and then heated with dilute HCl to yield N-methyl - 3,4 - methylenedioxyaniline hydrochloride which on treatment with dichloracetyl chloride gives dichloracet - 3,4 - methylene dioxy - N - methylanilide; dichloracet - 4 - hydroxy - N - methylanilide is nitrated to the corresponding 3-nitro derivative and reduced with stannous chloride to the 3-amino derivative; similar reduction of dichloracet-N-methyl-4-nitroanilide yields the corresponding 4-amino compound; dichloracet - 4 - hydroxy - 3 - nitro - N - methylanilide is further nitrated with fuming nitric to yield dichloracet - 4 - hydroxy - 3,5 - dinitro - N-methylanilide. Starting materials. 3,4 - Dihydroxy - N - methylaniline hydrobromide is prepared by refluxing 3,4-dimethoxy-N-methylaniline hydrochloride with aqueous HBr; 3,5-dihydroxy-N-ethylaniline is obtained by treating phloroglucinol with aqueous ethylamine; and N-methyl-m-anisidine by refluxing form-m-anisidide with potassium hydroxide in acetone and then with methyl iodide, finally hydrolysing the product with hydrochloric acid and liberating the base with alkali. Other intermediates similarly prepared from the corresponding formylated amines are the hydrochlorides of 4 - methoxy - n - propyl-, 4 - n - propoxy - N - methyl-, 4 - allyloxy - N - methyl-, 4 - phenoxy - N - methyl - 2 - methoxy - N - methyl and 2-butoxy -N-methyl-aniline. The third Provisional Specification further refers to compounds of the above general formula wherein R1 and R2 of the -NR1R2 substituent may represent aralkyl or aryl radicals.
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB21458/54A GB767148A (en) | 1954-07-22 | 1954-07-22 | New acetanilide derivatives and the manufacture thereof |
NL199019A NL94534C (en) | 1954-07-22 | 1955-07-19 | METHOD FOR PREPARING AMOEBICIDE, N.N-DIGESUBSTITUATED DICHLORACETAMIDES |
US523110A US2912438A (en) | 1954-07-22 | 1955-07-19 | New acetanilides derivatives and the manufacture thereof |
DK241855AA DK89390C (en) | 1954-07-22 | 1955-07-20 | Process for the preparation of dichloroacetanilide derivatives. |
DEB36568A DE1046063B (en) | 1954-07-22 | 1955-07-21 | Process for the production of new, amoebicidal acetanilides |
CH336368D CH336368A (en) | 1954-07-22 | 1955-07-22 | Process for the preparation of dichloroacetanilide derivatives |
MY41/57A MY5700041A (en) | 1954-07-22 | 1957-12-30 | New acetanilide derivatives and the manufacture thereof |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB21458/54A GB767148A (en) | 1954-07-22 | 1954-07-22 | New acetanilide derivatives and the manufacture thereof |
GB2703054 | 1954-09-17 | ||
GB862555 | 1955-03-24 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB767148A true GB767148A (en) | 1957-01-30 |
Family
ID=27255236
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB21458/54A Expired GB767148A (en) | 1954-07-22 | 1954-07-22 | New acetanilide derivatives and the manufacture thereof |
Country Status (6)
Country | Link |
---|---|
CH (1) | CH336368A (en) |
DE (1) | DE1046063B (en) |
DK (1) | DK89390C (en) |
GB (1) | GB767148A (en) |
MY (1) | MY5700041A (en) |
NL (1) | NL94534C (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1145634B (en) * | 1957-11-08 | 1963-03-21 | Boots Pure Drug Co Ltd | Process for the preparation of esters of p-hydroxy-N-dichloroacet-N-methylanilide |
DE1148560B (en) * | 1957-11-08 | 1963-05-16 | Boots Pure Drug Co Ltd | Process for the preparation of amoebicidally active esters of p-hydroxy-N-dichloroacet-N-methylanilide |
CN114773209A (en) * | 2022-05-05 | 2022-07-22 | 江苏常隆农化有限公司 | Method for recovering N-methylaniline from mefenacet recrystallization mother liquor |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4098760A (en) * | 1977-01-13 | 1978-07-04 | Uniroyal, Inc. | Substituted haloacetamide antioxidants for elastomers and plastic polymers |
-
1954
- 1954-07-22 GB GB21458/54A patent/GB767148A/en not_active Expired
-
1955
- 1955-07-19 NL NL199019A patent/NL94534C/en active
- 1955-07-20 DK DK241855AA patent/DK89390C/en active
- 1955-07-21 DE DEB36568A patent/DE1046063B/en active Pending
- 1955-07-22 CH CH336368D patent/CH336368A/en unknown
-
1957
- 1957-12-30 MY MY41/57A patent/MY5700041A/en unknown
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1145634B (en) * | 1957-11-08 | 1963-03-21 | Boots Pure Drug Co Ltd | Process for the preparation of esters of p-hydroxy-N-dichloroacet-N-methylanilide |
DE1148560B (en) * | 1957-11-08 | 1963-05-16 | Boots Pure Drug Co Ltd | Process for the preparation of amoebicidally active esters of p-hydroxy-N-dichloroacet-N-methylanilide |
CN114773209A (en) * | 2022-05-05 | 2022-07-22 | 江苏常隆农化有限公司 | Method for recovering N-methylaniline from mefenacet recrystallization mother liquor |
Also Published As
Publication number | Publication date |
---|---|
DK89390C (en) | 1960-07-25 |
NL94534C (en) | 1960-06-15 |
DE1046063B (en) | 1958-12-11 |
CH336368A (en) | 1959-04-15 |
MY5700041A (en) | 1957-12-31 |
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