Potassium Fluoride → HCID 18922599, compound

HRID 1289860Notes

Reaction equation

HRID 1289860 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12](=[O:13])[CH2:11][C:10]([C:14]([F:17])([F:16])[F:15])=[N:9]1.Br[CH2:19][N:20]1[C:24](=[O:25])[C:23]2[C:26]([CH:32]([CH3:34])[CH3:33])=[CH:27][C:28]([O:30][CH3:31])=[CH:29][C:22]=2[S:21]1(=[O:36])=[O:35].[F-].[K+]>CN(C=O)C.O>[CH:32]([C:26]1[C:23]2[C:24](=[O:25])[N:20]([CH2:19][O:13][C:12]3[N:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[Cl:1])[N:9]=[C:10]([C:14]([F:17])([F:15])[F:16])[CH:11]=3)[S:21](=[O:36])(=[O:35])[C:22]=2[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=1)([CH3:34])[CH3:33]

Participants

6

Reactant 3

HCID 522689Potassium FluorideHCID 108825772-bromomethyl-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxideHCID 14042797HCID 14042797, compound

Product 1

HCID 18922599HCID 18922599, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture 2,4-dihydro-2-(2-chlorophenyl)-5-trifluoromethyl-3H-pyrazol-3-one (543 mg; 2.06 mmol), 2-bromomethyl-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (600 mg, 1.72 mmol) and KF (250 mg, 3.44 mmol) in 7 ml of DMF was stirred at room temperature for 4 hours. The mixture was diluted with water, extracted with ether (3×), and the organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (2×, silica gel; 12-50% ethyl acetate in hexane; 10-50% methylene chloride/ethyl acetate) and recrystallized from ethyl acetate/hexane to afford 392 mg (43%) of 4-isopropyl-6-methoxy-2-[1-(2-chlorophenyl)-3-trifluoromethylpyrazol-5-yl-oxymethyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (Formula I: R1 =2-Cl--Ph; R2 =CF3 ; R3 =H; R4 =CH(CH3)2 ; R5 =6-OCH3) as m.p. 134-1360° C.

Workup

  1. extractionextracted with ether (3×)
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography (2×, silica gel; 12-50% ethyl acetate in hexane; 10-50% methylene chloride/ethyl acetate)
  5. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-d37b723f75e64a7ba0ccb7a9b16fd894
Source dataset
uspto-grants-1998_05
Patent number
US05750550

Reaction notes

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