GB1016826A - Acylamino compounds and a process for preparing them - Google Patents
Acylamino compounds and a process for preparing themInfo
- Publication number
- GB1016826A GB1016826A GB1225/63A GB122563A GB1016826A GB 1016826 A GB1016826 A GB 1016826A GB 1225/63 A GB1225/63 A GB 1225/63A GB 122563 A GB122563 A GB 122563A GB 1016826 A GB1016826 A GB 1016826A
- Authority
- GB
- United Kingdom
- Prior art keywords
- radical
- alkyl
- aryl
- cycloalkyl
- alkenyl
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/267—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/64—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups singly-bound to oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms directly attached in position 2
- C07D239/10—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/06—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings
- C07D265/08—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D265/10—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with oxygen atoms directly attached to ring carbon atoms
Abstract
The invention comprises acylamino compounds of the general formulae <FORM:1016826/C2/1> iu which R is a hydrogen atom or an alkyl, alkenyl, cycloalkyl, aryl, or methoxymethyl; R1 is a hydrogen atom or an alkyl, alkenyl, cycloalkyl, or aryl radical; R11 is a methyl, dihalomethyl, isopropenyl, cycloalkyl, aryl, alkoxy, aryloxy, alkylamino or arylamino radical; Y is a haloethyl, alkoxyethyl, a carboxylic acyloxyethyl, alkoxyalkenyl or alkenyl group containing 2 to 4 carbon atoms, said ethyl and alkenyl groups being substituted by alkyl and/or aryl radicals; Z is an -O- or -NH- radical; and R2 is a hydrogen atom, an alkyl radical of 1 to 4 carbons, a cycloalkyl or aryl radical. These compounds may be made by reacting a derivative of an acylated amine, of the formula <FORM:1016826/C2/2> in which X is a halogen atom, an acyloxy, alkoxy or aryloxy radical and R, R1 and R11 have the meanings above, with a compound which contains a > C = C < double bond, or a product which reacts as a conjugated diene in a diene synthesis, and separating the product formed from the reaction mixture. The starting material may be an olefine of the general formula <FORM:1016826/C2/3> wherein R12 is a hydrogen atom, an alky radical having 1 to 4 carbon atoms, an alkenyl radical of 1 to 4 carbon atoms, a cycloalkyl radical, an aryl radical or a vinylaryl radical or two radicals together form a cycloaliphatic ring. The reaction may be effected without a catalyst or in the presence of a Lewis-acid or an organic sulphonic acid in an amount up to 20 mol. per cent of the acylated amine derivative, said reaction being carried out under anhydrous conditions in a non-polar solvent at a temperature of from -40 DEG to 180 DEG C. Methods for making the acylated amine starting materials are outlined. Alkoxymethyl carbamic acid esters may be made from alkoxy acetamides with bromine and alkali metal alcoholates, or from alkoxy acetic acid azide with absolute alcohol. The hydroxymethyl derivatives are obtained from aqueous formaldehyde solution and carbamic acid esters. Examples are given of the preparation of N-alkyl-N-chloromethyl carbamic esters from 1,3,3-trimethyl-hexahydro-s-triazine and chloroformic esters; alkoxymethyl carbamic esters from N-alkyl-N-chloromethylcarbamic acid chlorides and sodium alcoholates; or from carbamic acid ethyl ester, formaldehyde and an alcohol; N-chloromethyl-N-acyl-amines are made from 1,3,5-trimethylhexahydro-s-triazine and an acid chloride. N - alkyl - N - acyloxymethyl carboxylic acid amides are made from the above triazines and carboxylic acid anhydrides. N-alkyl-N-a -acyloxyalkyl carbamic esters or carbonamides are made from N-alkyl-N-haloalkyl carbamic esters or carbonamides and alkali metal salts of carboxylic acids. Detailed examples of the preparation of the novel acylamino compounds are given.ALSO:Herbicidal action is shown in aqueous emulsion by acylamino compounds of the general formulae <FORM:1016826/A5-A6/1> in which R is a hydrogen atom or an alkyl, alkenyl, cycloalkyl, aryl or methoxymethyl, R1 is a hydrogen atom or an alkyl, alkenyl, cycloalkyl or aryl radical; R11 is a methyl, dihalomethyl, isopropenyl, cycloalkyl, aryl, alkoxy, aryloxy, alkylamino or arylamino radical; Y is a haloethyl, alkoxyethyl, a carboxylic acyloxyethyl, alkoxyalkenyl or alkenyl group containing 2 to 4 carbon atoms, said ethyl and alkenyl groups being substituted by alkyl and/or aryl radicals; Z is an -O- or -NH- radical; and R2 is a hydrogen atom, an alkyl radical of 1 to 4 carbons, a cycloalkyl or aryl radical.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF35737A DE1212532B (en) | 1962-01-10 | 1962-01-10 | Process for the preparation of acyclic and / or cyclic carboxamides |
DE140962X | 1962-09-14 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1016826A true GB1016826A (en) | 1966-01-12 |
Family
ID=25751979
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1225/63A Expired GB1016826A (en) | 1962-01-10 | 1963-01-10 | Acylamino compounds and a process for preparing them |
Country Status (4)
Country | Link |
---|---|
BE (1) | BE626980A (en) |
CH (1) | CH428700A (en) |
DE (1) | DE1212532B (en) |
GB (1) | GB1016826A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2077528A1 (en) * | 1969-11-20 | 1971-10-29 | Sandoz Sa | |
US8007849B2 (en) | 2005-12-14 | 2011-08-30 | International Flavors & Fragrances Inc. | Unsaturated cyclic and acyclic carbamates exhibiting taste and flavor enhancement effect in flavor compositions |
WO2012046070A1 (en) | 2010-10-06 | 2012-04-12 | Richardvince.Com Limited | Protective apparel for martial arts training |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5384315A (en) * | 1994-02-14 | 1995-01-24 | Uniroyal Chemical Company, Inc. | Thiophene substituted cycloamines, compositions and use |
DE4407182A1 (en) * | 1994-03-04 | 1995-09-07 | Bayer Ag | N-acyloxyalkyl carboxamides and process for their preparation |
-
0
- BE BE626980D patent/BE626980A/xx unknown
-
1962
- 1962-01-10 DE DEF35737A patent/DE1212532B/en active Pending
- 1962-12-24 CH CH1510262A patent/CH428700A/en unknown
-
1963
- 1963-01-10 GB GB1225/63A patent/GB1016826A/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2077528A1 (en) * | 1969-11-20 | 1971-10-29 | Sandoz Sa | |
US8007849B2 (en) | 2005-12-14 | 2011-08-30 | International Flavors & Fragrances Inc. | Unsaturated cyclic and acyclic carbamates exhibiting taste and flavor enhancement effect in flavor compositions |
WO2012046070A1 (en) | 2010-10-06 | 2012-04-12 | Richardvince.Com Limited | Protective apparel for martial arts training |
Also Published As
Publication number | Publication date |
---|---|
DE1212532B (en) | 1966-03-17 |
BE626980A (en) | |
CH428700A (en) | 1967-01-31 |
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