GB792490A - Substituted phenoxyacetic amides - Google Patents
Substituted phenoxyacetic amidesInfo
- Publication number
- GB792490A GB792490A GB18205/56A GB1820556A GB792490A GB 792490 A GB792490 A GB 792490A GB 18205/56 A GB18205/56 A GB 18205/56A GB 1820556 A GB1820556 A GB 1820556A GB 792490 A GB792490 A GB 792490A
- Authority
- GB
- United Kingdom
- Prior art keywords
- eugenol
- glycollic acid
- alkyl
- formula
- isoeugenol
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises eugenol- and isoeugenol-glycollic acid amides of the formula <FORM:0792490/IV (b)/1> wherein R is an allyl or propen-(1)-yl radical, R1 is an alkyl, alkenyl or cycloalkyl radical or a phenyl or benzyl radical optionally carrying halogen or lower (1-4C) alkyl or alkoxy substituents, and R2 is hydrogen or an alkyl or alkenyl radical. The compounds are prepared by (1) treating eugenol- or isoeugenol-glycollic acid or a reactive functional derivative thereof such as a halide, a mixed anhydride formed with a lower organic carboxylic acid or an ester such as a lower alkyl or phenyl ester, with a primary or secondary amine of the formula HN(R1)R2, preferably in a solvent or diluent and, in the reactions with halides or mixed anhydrides, in the presence of a tertiary organic base or an excess of the amine to be reacted, as an acidbinding agent; (2) reacting a carbamyl chloride of the formula Cl-CO-N(R1)R2 in which R1 has the meaning previously given and R2 has the meaning previously given, but cannot be hydrogen, with a salt, preferably an alkali-metal salt, of eugenol- or isoeugenol-glycollic acid; or (3) partial hydrolysis of an amidine of the general formula <FORM:0792490/IV (b)/2> Many suitable amine starting materials of the formula HN(R1)R2 are specified. Examples describe the preparation of eugenol-glycollic acid diethylamide, methylamide, ethylamide, n-propylamide, di-n-propylamide, di-n-butylamide, N-methyl-isopropylamide, isopropylamide, allylamide, n-butylamide, anilide, cyclohexylamide, cyclohexylmethylamide, N-methylcyclohexylamide, benzylamide, piperidide, morpholide, pyrrolidide, dimethylamide, the N-n-butyl-, methyl-, ethyl-, n-propyl-, n-amyl-, n-hexyl-, allyl- and methylallyl anilides and various N-alkyl toluidides, 31:41 - dimethylanilides, chloranilides, bromanilides and anisidides, and isoeugenol-glycollic acid diethylamide, N-ethyl anilide and N-n-butyl anilide. Starting materials. 2-Methoxy-4-allylphenoxyacetyl chloride (eugenol-glycollic acid chloride) is made by the reaction of eugenol-glycollic acid with thionyl chloride.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH792490X | 1955-06-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB792490A true GB792490A (en) | 1958-03-26 |
Family
ID=4537072
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB18205/56A Expired GB792490A (en) | 1955-06-14 | 1956-06-13 | Substituted phenoxyacetic amides |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB792490A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1151793B (en) * | 1958-07-30 | 1963-07-25 | Geigy Ag J R | Process for the preparation of therapeutically active phenoxyacetic acid amides |
| DE1152402B (en) * | 1958-07-30 | 1963-08-08 | Geigy Ag J R | Process for the preparation of therapeutically active phenoxyacetic acid amides |
| US3141757A (en) * | 1959-07-28 | 1964-07-21 | Rhone Poulenc Sa | Herbicidal phenoxyacetamides |
| RU2660654C1 (en) * | 2017-06-09 | 2018-07-09 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Волгоградский государственный технический университет" (ВолгГТУ) | N-(adamantan-2-yl)- and n-[(adamantan-1-yl)methyl]- derivatives of 2-(4-allyl-2-methoxyphenoxy)acetic acid amide, which are potential synthetic adaptogens of emergency action |
-
1956
- 1956-06-13 GB GB18205/56A patent/GB792490A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1151793B (en) * | 1958-07-30 | 1963-07-25 | Geigy Ag J R | Process for the preparation of therapeutically active phenoxyacetic acid amides |
| DE1152402B (en) * | 1958-07-30 | 1963-08-08 | Geigy Ag J R | Process for the preparation of therapeutically active phenoxyacetic acid amides |
| US3141757A (en) * | 1959-07-28 | 1964-07-21 | Rhone Poulenc Sa | Herbicidal phenoxyacetamides |
| RU2660654C1 (en) * | 2017-06-09 | 2018-07-09 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Волгоградский государственный технический университет" (ВолгГТУ) | N-(adamantan-2-yl)- and n-[(adamantan-1-yl)methyl]- derivatives of 2-(4-allyl-2-methoxyphenoxy)acetic acid amide, which are potential synthetic adaptogens of emergency action |
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