Potassium Fluoride → HCID 67639973, compound

HRID 1289851Notes

Reaction equation

HRID 1289851 reaction equation
[C:1]1([N:7]2[C:11](=[O:12])[CH2:10][C:9]([Cl:13])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:15][N:16]1[C:20](=[O:21])[C:19]2[C:22]([CH:28]([CH3:30])[CH3:29])=[CH:23][C:24]([O:26][CH3:27])=[CH:25][C:18]=2[S:17]1(=[O:32])=[O:31].[F-].[K+]>CN(C=O)C>[CH:28]([C:22]1[C:19]2[C:20](=[O:21])[N:16]([CH2:15][O:12][C:11]3[N:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[N:8]=[C:9]([Cl:13])[CH:10]=3)[S:17](=[O:32])(=[O:31])[C:18]=2[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=1)([CH3:30])[CH3:29]

Participants

5

Reactant 3

HCID 522689Potassium FluorideHCID 108825772-bromomethyl-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxideHCID 18922596HCID 18922596, compound

Product 1

HCID 67639973HCID 67639973, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture 2,4-dihydro-2-phenyl-5-chloro-3H-pyrazol-3-one (350 mg; 1.8 mmol), 2-bromomethyl-4-isopropyl-6-methoxy-1,2-benziso thiazol-3(2H)-one 1,1-dioxide (686 mg, 1.98 mmol), and KF (209 mg; 3.6 mmol) in DMF (8 ml) was stirred at 20° C. for 3 hours and the mixture was diluted with ice water. The above mixture was extracted with ether (3×) and the organic layer was dried over sodium sulfate, and concentrated in vacuo. The residue was purified by column chromatography (silica gel; 25-50% ethyl acetate/hexane; methylene chloride/hexane, 20-100%) and recrystallized from ethyl acetate/hexane to afford 265 mg (32%) of 4-isopropyl-6-methoxy-2-(1-phenyl-3-chloropyrazol-5-yl-oxymethyl)-1,2-benzisothiazol-3(2H)-one 1, 1-dioxide (Formula I: R1 =phenyl; R2 =Cl; R3 =H; R4 =CH(CH3)2 ; R5 =6-OCH3) as a white solid, m.p. 109°-110° C.

Workup

  1. extractionThe above mixture was extracted 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 (silica gel; 25-50% ethyl acetate/hexane; methylene chloride/hexane, 20-100%)
  5. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-f534ce8a6ca94fcabeeb880074c97b63
Source dataset
uspto-grants-1998_05
Patent number
US05750550

Reaction notes

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