Water → HCID 18922591, compound

HRID 1289825Notes

Reaction equation

HRID 1289825 reaction equation
[CH3:1][N:2]1[C:6](=[O:7])[CH2:5][C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:3]1.[F-].[K+].Cl[CH2:17][N:18]1[C:22](=[O:23])[C:21]2[C:24]([CH:30]([CH3:32])[CH3:31])=[CH:25][C:26]([O:28][CH3:29])=[CH:27][C:20]=2[S:19]1(=[O:34])=[O:33].O>CN(C=O)C>[CH:30]([C:24]1[C:21]2[C:22](=[O:23])[N:18]([CH2:17][O:7][C:6]3[N:2]([CH3:1])[N:3]=[C:4]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[CH:5]=3)[S:19](=[O:34])(=[O:33])[C:20]=2[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=1)([CH3:32])[CH3:31]

Participants

6

Reactant 4

HCID 962WaterHCID 1425623H-Pyrazol-3-one, 2,4-dihydro-2-methyl-5-phenyl-HCID 522689Potassium FluorideHCID 99951732-(Chloromethyl)-4-isopropyl-6-methoxybenzo[D]isothiazol-3(2H)-one 1,1-dioxide

Product 1

HCID 18922591HCID 18922591, compoundYield 27.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,4-dihydro-2-methyl-5-phenyl-3H-pyrazol-3-one (0.63 g; 3.62 mmol) in DMF (20 ml) was added 230 mg (3.96 mmol) of KF followed by 2-chloromethyl-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (1 g, 3.29 mmol) and the resulting mixture was stirred at room temperature for 24 hours and then poured into water. The above mixture was extracted with ethyl acetate and the organic layer was washed with water, brine, dried, and concentrated in vacuo. The residue was purified by flash chromatography to afford 0.4 g (27%) of 4-isopropyl-6-methoxy-2-(1-methyl-3-phenylpyrazol-5-yl-oxymethyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (Formula I: R1 =CH3 ; R2 =Ph; R3 =H; R4 =CH(CH3)2 ; R5 =6-OCH3) as a white solid, m.p. 126°-128° C.

Workup

  1. extractionThe above mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with water, brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-3961f2033b4d48a6b0499087f4e23858
Source dataset
uspto-grants-1998_05
Patent number
US05750550

Reaction notes

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