Dimethylformamide → 4-isopropyl-6-methoxy-2-(1-phenyl-3-trifluoromethyl-4-chloropyrazol-5-yl-oxymethyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxide

HRID 1289843Notes

Reaction equation

HRID 1289843 reaction equation
[C:1]1([N:7]2[CH:11]=[C:10]([Cl:12])[C:9]([C:13]([F:16])([F:15])[F:14])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:18][N:19]1[C:23](=[O:24])[C:22]2[C:25]([CH:31]([CH3:33])[CH3:32])=[CH:26][C:27]([O:29][CH3:30])=[CH:28][C:21]=2[S:20]1(=[O:35])=[O:34].[F-].[K+].CN(C=[O:42])C>O>[CH:31]([C:25]1[C:22]2[C:23](=[O:24])[N:19]([CH2:18][O:42][C:11]3[N:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[N:8]=[C:9]([C:13]([F:16])([F:15])[F:14])[C:10]=3[Cl:12])[S:20](=[O:35])(=[O:34])[C:21]=2[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=1)([CH3:33])[CH3:32]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 522689Potassium FluorideHCID 108825772-bromomethyl-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxideHCID 189225581-Phenyl-3-trifluoromethyl-4-chloropyrazole

Product 1

HCID 189225904-isopropyl-6-methoxy-2-(1-phenyl-3-trifluoromethyl-4-chloropyrazol-5-yl-oxymethyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxideYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture 1-phenyl-3-trifluoromethyl-4-chloropyrazole (524 mg; 2 mmol), 2-bromomethyl-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (696 mg, 2 mmol), and KF (232 mg; 4 mmol) in DMF (8 ml) was stirred at 20° C. for 16 hours and the mixture was diluted with water. The above mixture was extracted with methylene chloride (3×) and the organic layer was dried over sodium sulfate, and concentrated in vacuo. The white residue was recrystallized from methylene chloride/hexane and purified by column chromatography (silica gel; 20% ethyl acetate/hexane; methylene chloride) to afford 730 mg (69%) of 4-isopropyl-6-methoxy-2-(1-phenyl-3-trifluoromethyl-4-chloropyrazol-5-yl-oxymethyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (Formula I: R1 =Ph; R2 =CF3 ; R3 =Cl; R4 =CH(CH3)2 ; R5 =6-OCH3) as a white solid, m.p. 185°-1870° C.

Workup

  1. extractionThe above mixture was extracted with methylene chloride (3×)
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe white residue was recrystallized from methylene chloride/hexane
  5. custompurified by column chromatography (silica gel; 20% ethyl acetate/hexane; methylene chloride)

Sources & evidence

ORD record
ord-334b843e459341e398e56f86396f0f2d
Source dataset
uspto-grants-1998_05
Patent number
US05750550

Reaction notes

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