Methanesulfonyl chloride → 1-((2-(2,4-Difluorophenyl)-3-methyl-2-oxiranyl)methyl)-1H-1,2,4-triazole

HRID 1654204Notes

Reaction equation

HRID 1654204 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:19])([CH:16](O)[CH3:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1.CS(Cl)(=O)=O>>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1([CH2:10][N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)[CH:16]([CH3:17])[O:19]1

Participants

3

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 14706433(2RS,3RS)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol

Product 1

HCID 147064491-((2-(2,4-Difluorophenyl)-3-methyl-2-oxiranyl)methyl)-1H-1,2,4-triazole

Procedure

In a manner like that described in Reference Example 25, (2RS,3SR)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol (1.1 g) obtained in Reference Example 42 was allowed to react with methanesulfonyl chloride (0.35 ml), followed by treatment with a 28% sodium methylate methanol solution to afford (2RS,3RS)-2-(2,4-difluorophenyl)-3-methyl-2-(1H-1,2,4-triazol-1-yl)methyl oxirane. The product was purified by means of a silica gel column chromatography (ethyl acetate: methylene chloride=4:1) to give a yellow oily product (0.8 g).

Workup

  1. customobtained in Reference Example 42

Sources & evidence

ORD record
ord-6e770282dc834d15884520c4f22d3a97
Source dataset
uspto-grants-1995_04
Patent number
US05405861

Reaction notes

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