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

HRID 637991Notes

Reaction equation

HRID 637991 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[C:31]([Cl:32])=[CH:30][C:29]([N:33]=[C:34]=[O:35])=[CH:28][C:27]=2[Cl:36])=[N:17][CH:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:20]=1>>[Cl:14][C:15]1[C:16]([O:25][C:26]2[C:31]([Cl:32])=[CH:30][C:29]([NH:33][C:34]([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:35])=[CH:28][C:27]=2[Cl:36])=[N:17][CH:18]=[C:19]([C:21]([F:23])([F:24])[F:22])[CH:20]=1

Participants

3

Reactant 2

HCID 13730259Ethyl 2,6-difluorobenzene-1-carboximidateHCID 139136133-Chloro-2-(2,6-dichloro-4-isocyanatophenoxy)-5-(trifluoromethyl)pyridine

Product 1

HCID 54449738ethyl N-[4-(3-chloro-5-trifluoromethylpyrid-2-yloxy)-3,5-dichlorophenylcarbamoyl]-2,6-difluorobenzimidate

Procedure

In a similar manner to that described in step (e) of Example I ethyl 2,6-difluorobenzimidate is reacted with 3-chloro-5-trifluoromethyl-2-(2,6-dichloro-4-isocyanatophenoxy)pyridine to give ethyl N-[4-(3-chloro-5-trifluoromethylpyrid-2-yloxy)-3,5-dichlorophenylcarbamoyl]-2,6-difluorobenzimidate (Compound IV). The intermediate isocyanate is obtained by the procedure of step (c) of Example 1 from 2-(4-amino-2,6-dichlorophenoxy)-3-chloro-5-trifluoromethylpyridine. This compound is described in Japanese published patent application No. 79-125699 (Chemical Abstracts, vol. 92, 146618d).

Sources & evidence

ORD record
ord-602dbcfcced84a2f848be0e8898aadc6
Source dataset
uspto-grants-1985_12
Patent number
US04559353

Reaction notes

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