Epibromohydrin → 5-(3-Chloro-5-trifluoromethylpyridin-2-yl)-3-(2,3-epoxypropyl)-1-(1-methylethyl)benzimidazol-2-one

HRID 1276084Notes

Reaction equation

HRID 1276084 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.ClC1C(C2C=CC3N(C(C)C)C(=O)NC=3C=2)=NC=C(C(F)(F)F)C=1.C([CH:52]1[O:54][CH2:53]1)Br>>[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][CH:53]4[O:54][CH2:52]4)[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 18430EpibromohydrinHCID 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 221148665-(3-Chloro-5-trifluoromethylpyridin-2-yl)-3-(2,3-epoxypropyl)-1-(1-methylethyl)benzimidazol-2-oneYield 83%

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-trifluoromethyl-pyridin-2yl)-1-(1-methylethyl)benzimidazol-2-one and 1.0 g of epibromohydrin gave 2.4 g of colorless crystals. Yield: 83%; m.p.: 110-111° C.

Sources & evidence

ORD record
ord-ab7dc3feb84c49e78dd539e329cca87d
Source dataset
uspto-grants-2000_12
Patent number
US06165941

Reaction notes

Loading…