Chlorosuccinimide → HCID 86589689, compound

HRID 1828371Notes

Reaction equation

HRID 1828371 reaction equation
[CH3:1][C:2]([NH:8][C:9]([C:11]1[CH:31]=[CH:30][CH:29]=[CH:28][C:12]=1[C:13]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][C:17]=1[CH3:27])=[O:14])=[O:10])([CH3:7])[CH:3]=[N:4][O:5][CH3:6].BrN1C(=O)CCC1=O.[Cl:40]N1C(=O)CCC1=O>>[Cl:40][C:31]1[C:11]([C:9]([NH:8][C:2]([CH3:1])([CH3:7])[CH:3]=[N:4][O:5][CH3:6])=[O:10])=[C:12]([CH:28]=[CH:29][CH:30]=1)[C:13]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]([F:24])([F:25])[F:26])=[CH:18][C:17]=1[CH3:27])=[O:14]

Participants

4

Reactant 3

HCID 31398ChlorosuccinimideHCID 67184N-bromobutanimideHCID 86589690HCID 86589690, compound

Product 1

HCID 86589689HCID 86589689, compoundYield 63%

Procedure

2-(1,1-Dimethyl-2-(N-methoxyimino)ethylaminocarbonyl)-2′-methyl-4′-trifluoromethoxybenzanilide was treated in the same manner as in Example 36, except that the N-bromosuccinimide was replaced with N-chlorosuccinimide, to obtain 3-chloro-2-(1,1-dimethyl-2-(N-methoxyimino)ethylaminocarbonyl)-2′-methyl-4′-trifluoromethoxybenzanilide (yield 63%, melting point 197° C.). Regioselectivity of chlorination into the 3-position was 100%.

Sources & evidence

ORD record
ord-0c8391b69820495a9cb3acf4fbe8ffb4
Source dataset
uspto-grants-2006_06
Patent number
US07057067B2

Reaction notes

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