Methanesulfenyl chloride, trifluoro- → 3-Acetyl-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-methylsulfinyl-5-trifluoromethylsulfenylaminopyrazole

HRID 2186116Notes

Reaction equation

[C:1]([C:4]1[C:8]([S:9]([CH3:11])=[O:10])=[C:7]([NH2:12])[N:6]([C:13]2[C:18]([Cl:19])=[CH:17][C:16]([C:20]([F:23])([F:22])[F:21])=[CH:15][C:14]=2[Cl:24])[N:5]=1)(=[O:3])[CH3:2].C(N(C(C)C)CC)(C)C.[F:34][C:35]([F:39])([F:38])[S:36]Cl>ClCCl>[C:1]([C:4]1[C:8]([S:9]([CH3:11])=[O:10])=[C:7]([NH:12][S:36][C:35]([F:39])([F:38])[F:34])[N:6]([C:13]2[C:14]([Cl:24])=[CH:15][C:16]([C:20]([F:22])([F:21])[F:23])=[CH:17][C:18]=2[Cl:19])[N:5]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of 3-acetyl-5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-methylsulfinylpyrazole (3 g) in dichloromethane containing diisopropylethylamine (1.44 ml) was added trifluoromethylsulfenyl chloride (0.97 ml) at −30° C. The mixture was stirred (2 hours) and when at 20° C. purged with nitrogen. Water was added and the organic phase dried (sodium sulfate) and evaporated. The residue was purified by silica gel chromatography eluting with 25% ethyl acetate in hexane to give 3-acetyl-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-methylsulfinyl-5-trifluoromethylsulfenylaminopyrazole (Compound 10, 0.5 g), m.p. 67-102° C., mass spectral analysis M+/e=499.

Workup

custompurged with nitrogen
additionWater was added
dry with materialthe organic phase dried (sodium sulfate)
customevaporated
customThe residue was purified by silica gel chromatography
washeluting with 25% ethyl acetate in hexane

Sources & evidence

ORD record: ord-a3197e39ec6840798d5146c605515e72
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06403628B1

Reaction notes

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