Ethyl 2,6-difluorobenzene-1-carboximidate → ethyl N-[4-(3-chloro-5-trifluoromethylpyrid-2-yloxy)phenylcarbamoyl]-2,6-difluorobenzimidate

HRID 637990Notes

Reaction equation

[F:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:3]=1[C:4](=[NH:8])[O:5][CH2:6][CH3:7].[Cl:14][C:15]1[C:16]([O:25][C:26]2[CH:31]=[CH:30][C:29]([N:32]=[C:33]=[O:34])=[CH:28][CH:27]=2)=[N:17][CH:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:20]=1>C(OCC)C>[Cl:14][C:15]1[C:16]([O:25][C:26]2[CH:31]=[CH:30][C:29]([NH:32][C:33]([N:8]=[C:4]([O:5][CH2:6][CH3:7])[C:3]3[C:2]([F:1])=[CH:12][CH:11]=[CH:10][C:9]=3[F:13])=[O:34])=[CH:28][CH:27]=2)=[N:17][CH:18]=[C:19]([C:21]([F:24])([F:22])[F:23])[CH:20]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of ethyl 2,6-difluorobenzimidate (0.14 g), 3-chloro-5-trifluoromethyl-2-(4-isocyanatophenoxy)pyridine (0.24 g), and diethyl ether (10 ml) was stirred at 20° C. for 18 hours, after which the solvent was removed by evaporation and the residual solid recrystallised from petroleum ether (boiling range 60°-80° C.) to yield ethyl N-[4-(3-chloro-5-trifluoromethylpyrid-2-yloxy)phenylcarbamoyl]-2,6-difluorobenzimidate as a white solid (0.29 g), m.p. 127°-130° C.

Workup

customafter which the solvent was removed by evaporation
customthe residual solid recrystallised from petroleum ether (boiling range 60°-80° C.)

Sources & evidence

ORD record: ord-5d7e54a2d27b4eca99f4bb2888135c61
Source dataset: uspto-grants-1985_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04559353

Reaction notes

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