Cesium → 4,6-diethoxy-2-[1-phenyl-3-trifluoromethylpyrazol-5-yl-oxymethyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxide

HRID 1289880Notes

Reaction equation

HRID 1289880 reaction equation
[Cs].[C:2]1([N:8]2[C:12]([OH:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[N:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:19][N:20]1[C:24](=[O:25])[C:23]2[C:26]([O:33][CH2:34][CH3:35])=[CH:27][C:28]([O:30][CH2:31][CH3:32])=[CH:29][C:22]=2[S:21]1(=[O:37])=[O:36]>CN(C=O)C>[CH2:34]([O:33][C:26]1[C:23]2[C:24](=[O:25])[N:20]([CH2:19][O:13][C:12]3[N:8]([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[N:9]=[C:10]([C:14]([F:16])([F:17])[F:15])[CH:11]=3)[S:21](=[O:37])(=[O:36])[C:22]=2[CH:29]=[C:28]([O:30][CH2:31][CH3:32])[CH:27]=1)[CH3:35]

Participants

5

Reactant 3

HCID 5354618CesiumHCID 538174362-chloromethyl-4, 6-diethoxy-1,2-benzisothiazol-3 (2H)-one 1,1-dioxideHCID 178516151HCID 178516151, compound

Product 1

HCID 189226094,6-diethoxy-2-[1-phenyl-3-trifluoromethylpyrazol-5-yl-oxymethyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxideYield 714.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The cesium salt of 1-phenyl-3-trifluoromethyl-5-hydroxypyrazole [prepared from 1-phenyl-3-trifluoromethyl-5-hydroxypyrazole (0.714 g, 0.312 mmol) and Cs2CO3 (0.509 g, 0.156 mmol)] was suspended in DMF (20 ml) and treated with 2-chloromethyl-4, 6-diethoxy-1,2-benzisothiazol-3 (2H)-one 1,1-dioxide (0.5 g, 0.156 mmol). The reaction mixture was stirred at room temperature for 24 hours, then was poured onto ice-water and was extracted with ethyl acetate (300 mL). The organic layer was washed with water, then brine and then was dried over MgSO4. The solvent was removed and the residue was purified by flash chromatography on silica gel eluting with CH2Cl2 to afford 0.57 g (71%) of 4,6-diethoxy-2-[1-phenyl-3-trifluoromethylpyrazol-5-yl-oxymethyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (Formula I: R1 =Ph; R2 =CF3 ; R3 =H; R4 =OEt; R5 =6-OEt), m.p. 159°-160° C.

Workup

  1. additionwas poured onto ice-water
  2. extractionwas extracted with ethyl acetate (300 mL)
  3. washThe organic layer was washed with water
  4. dry with materialbrine and then was dried over MgSO4
  5. customThe solvent was removed
  6. customthe residue was purified by flash chromatography on silica gel eluting with CH2Cl2

Sources & evidence

ORD record
ord-399c4c1aa3d745c9bb5eb7fcec06b478
Source dataset
uspto-grants-1998_05
Patent number
US05750550

Reaction notes

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