Benzamide → Carbamic acid, ethyl ester
Reaction equation
C([NH2:9])(=O)C1C=CC=CC=1.[Cl:10][C:11]([O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:12]>>[Cl:10][C:11]([O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:12].[NH2:9][C:11]([O:13][CH2:14][CH3:19])=[O:12]Participants
Procedure
We have now discovered a method for the preparation of benzoylureas such as those disclosed in U.S. Pat. No. 3,748,356 and Belgian Pat. No. 833,288, which comprises the reaction of a benzamide, a C1 -C7 alkyllithium, a phenyl chloroformate and an amine. In one embodiment of the reaction, the benzamide is treated with the alkyllithium and a phenyl chloroformate in an inert solvent at a temperature of from about -80° to about -40° C. to form an intermediate urethane, the intermediate urethane is treated with an amine in an inert solvent at about -80° to about -40° C., and the temperature is slowly raised to from about 50° to about 100° C. to obtain the desired benzoylurea. In a second embodiment of the reaction, the benzamide is treated with the alkyllithium in an inert solvent at a temperature from about -80° to about -40° C. and the lithium salt so obtained is then treated with a carbamate at a temperature of about -80° to about -40° C., and the mixture is allowed to warm to from about 20° to about 40° C. to obtain the desired benzoylurea. The carbamate is obtained by the reaction of an amine with a phenyl chloroformate.
Workup
- customIn one embodiment of the reaction
Sources & evidence
- ORD record
- ord-c1d1bde92af74cb082deeaa5f51ce154
- Source dataset
- uspto-grants-1981_03
- Patent number
- USRE030563
Reaction notes
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