Bromoacetonitrile → 5-(3-Chloro-5-trifluoromethylpyridin-2-yl)-3-cyanomethyl-1-(1-methylethyl)benzimidazol-2-one

HRID 1276083Notes

Reaction equation

HRID 1276083 reaction equation
[Cl:1][C:2]1[C:3]([C:12]2[CH:25]=[CH:24][C:15]3[N:16]([CH:21]([CH3:23])[CH3:22])[C:17](=[O:20])[N:18]([CH3:19])[C:14]=3[CH:13]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.ClC1[C:28](C2C=CC3N(C(C)C)C(=O)NC=3C=2)=[N:29]C=C(C(F)(F)F)C=1.BrCC#N>>[Cl:1][C:2]1[C:3]([C:12]2[CH:25]=[CH:24][C:15]3[N:16]([CH:21]([CH3:22])[CH3:23])[C:17](=[O:20])[N:18]([CH2:19][C:28]#[N:29])[C:14]=3[CH:13]=2)=[N:4][CH:5]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:7]=1

Participants

4

Reactant 3

HCID 11534BromoacetonitrileHCID 221148405-(3-Chloro-5-trifluoromethylpyridin-2-yl)-3-methyl-1-(1-methylethyl)benzimidazol-2-oneHCID 221148555-(3-Chloro-5-trifluoromethylpyridin-2yl)-1-(1-methylethyl)benzimidazol-2-one

Product 1

HCID 221148585-(3-Chloro-5-trifluoromethylpyridin-2-yl)-3-cyanomethyl-1-(1-methylethyl)benzimidazol-2-oneYield 50%

Procedure

In a similar manner to the preparation of 5-(3-chloro-5-trifluoromethylpyridin-2-yl)-3-methyl-1-(1-methylethyl)benzimidazol-2-one described above, 2.5 g of 5-(3-chloro-5-trifluoromethylpyridin-2-yl)-1-(1-methylethyl)benzimidazol-2-one and 0.9 g of bromoacetonitrile gave, after chromatography on silica gel, 1.4 g of colorless crystals. Yield: 50%; m.p.: 158-159° C.

Workup

  1. customgave

Sources & evidence

ORD record
ord-29d2c8a1456e4b3abfb488ed778d49d8
Source dataset
uspto-grants-2000_12
Patent number
US06165941

Reaction notes

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