Benzyl mercaptan → 5-(benzylsulphanyl)-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole

HRID 1843096Notes

Reaction equation

HRID 1843096 reaction equation
F[C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]([F:14])([F:13])[C:9]([F:12])([F:11])[F:10])[C:3]=1[C:15]([F:18])([F:17])[F:16].[CH2:19]([SH:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(CC)CC)C>C(#N)C>[CH2:19]([S:26][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]([F:14])([F:13])[C:9]([F:12])([F:11])[F:10])[C:3]=1[C:15]([F:18])([F:17])[F:16])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 8471TriethylamineHCID 135102735-Fluoro-1-methyl-3-pentafluoroethyl-4-trifluoromethyl-1H-pyrazole

Product 1

HCID 585425705-(benzylsulphanyl)-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazoleYield 78%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 3.00 g (10.5 mmol) of 5-fluoro-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole and 1.48 ml (12.6 mmol) of benzylmercaptan is initially introduced into 24 ml of acetonitrile at 0° C. 4.78 ml (34.3 mmol) of triethylamine are then added dropwise and the reaction mixture is stirred for two hours at between 0° C. and 10° C. Following concentration by evaporation in vacuo, the resulting oil is purified by chromatography on silica gel, giving 3.19 g of 5-(benzylsulphanyl)-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole (78%).

Workup

  1. concentrationconcentration
  2. customby evaporation in vacuo
  3. customthe resulting oil is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-db9efcc038d84ed1955de010cc103d1a
Source dataset
uspto-grants-2015_02
Patent number
US08946234B2

Reaction notes

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