Trifluoromethylsulfinylchloride → 5-amino-1-(2-chloro-6-fluoro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfinyl)-1H-pyrazole-3-carbonitrile

HRID 919169Notes

Reaction equation

[NH2:1][C:2]1[N:6]([C:7]2[C:12]([F:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[CH:3]=1.S(C1C=CC(C)=CC=1)(O)(=O)=O.CNC.[C:35]([S:39](Cl)=[O:40])([F:38])([F:37])[F:36]>C1(C)C=CC=CC=1>[NH2:1][C:2]1[N:6]([C:7]2[C:12]([F:13])=[CH:11][C:10]([C:14]([F:16])([F:15])[F:17])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[S:39]([C:35]([F:38])([F:37])[F:36])=[O:40]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 5-amino-1-(2-chloro-6-fluoro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile (140 g, 459.6 mmol, 1.00 eq.) and dimethylamine tosylate (151.8 g, 698.6 mmol, 1.52 eq.) in toluene (840 mL) was added CF3SOCl (89.7 g, 588.3 mmol, 1.28 eq.). After the mixture was stirred at 40° C. for 16 h, nitrogen was bubbled through the solution and the solution was cooled to rt. Then the mixture was poured into 2 L ice/water and stirred at 0° C. for 1 h. The precipitated solid was isolated by filtration and dried under vacuum. The solid was recrystallized with toluene to give 5-amino-1-(2-chloro-6-fluoro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfinyl)-1H-pyrazole-3-carbonitrile (125 g, 64%) as yellow solid.

Workup

customnitrogen was bubbled through the solution
temperaturethe solution was cooled to rt
additionThen the mixture was poured into 2 L ice/water
stirringstirred at 0° C. for 1 h
customThe precipitated solid was isolated by filtration
customdried under vacuum
customThe solid was recrystallized with toluene

Sources & evidence

ORD record: ord-9dac93fa030f492ba721f2b855d99919
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273007B2

Reaction notes

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