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Thionyl Chloride → 5-Amino-1-(6-bromo-1,1,3,3-tetrafluoro-1,3-dihydroisobenzofuran-5-yl)-3-cyano-4-trifluoromethylsulfinylpyrazole

HRID 1871566
Notes
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Reaction equation

HRID 1871566 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][C:15]=2[Br:16])[C:12]([F:18])([F:17])[O:11][C:10]3([F:20])[F:19])[N:5]=[C:4]([C:21]#[N:22])[CH:3]=1.[F:23][C:24]([F:29])([F:28])[S:25]([O-])=[O:26].[Na+].S(C1C=CC(C)=CC=1)(O)(=O)=O.CNC.S(Cl)(Cl)=O>C1(C)C=CC=CC=1.O>[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][C:15]=2[Br:16])[C:12]([F:18])([F:17])[O:11][C:10]3([F:20])[F:19])[N:5]=[C:4]([C:21]#[N:22])[C:3]=1[S:25]([C:24]([F:29])([F:28])[F:23])=[O:26]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 12199009Dimethylamine p-toluenesulfonateHCID 186915365-Amino-1-(6-bromo-1,1,3,3-tetrafluoro-1,3-dihydroisobenzofuran-5-yl)-3-cyanopyrazoleHCID 23690734Sodium trifluoromethanesulfinate

Product 1

HCID 186915245-Amino-1-(6-bromo-1,1,3,3-tetrafluoro-1,3-dihydroisobenzofuran-5-yl)-3-cyano-4-trifluoromethylsulfinylpyrazole
Yield 20.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
55 °C

Procedure

To a suspension wherein 5-amino-1-(6-bromo-1,1,3,3-tetrafluoro-1,3-dihydroisobenzofuran-5-yl)-3-cyanopyrazole (754 mg, 2.00 ml), sodium trifluoromethane-sulfinate (406 mg, 2.60 mmol) and dimethylamine tosylate (652 mg, 3.00 mmol) are in toluene (5 ml), thionyl chloride (309, mg, 2.60 mmol) was added dropwise under ice cooling over a period of about 10 minutes and then stirred under heating at 50 to 60° C. for 10 hours. After allowing time to cool, the reaction solution was poured into water, extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was subjected to silica gel column chromatography to give 200 mg of 5-amino-1-(6-bromo-1,1,3,3-tetrafluoro-1,3-dihydroisobenzofuran-5-yl)-3-cyano-4-trifluoromethylsulfinylpyrazole.

Workup

  1. temperatureto cool
  2. extractionextracted with ethyl acetate
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-13629306ba5346a2b571cc645e15a852
Source dataset
uspto-grants-2000_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06103750

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes