Water → 4-isopropyl-6-methoxy-2-[1-(4-nitrophenyl)-3-trifluoromethylpyrazol-5-yl-oxymethyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxide

HRID 1289838Notes

Reaction equation

HRID 1289838 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]([OH:15])=[CH:13][C:12]([C:16]([F:19])([F:18])[F:17])=[N:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:27][N:28]1[C:32](=[O:33])[C:31]2[C:34]([CH:40]([CH3:42])[CH3:41])=[CH:35][C:36]([O:38][CH3:39])=[CH:37][C:30]=2[S:29]1(=[O:44])=[O:43].O>CO.CN(C=O)C>[CH:40]([C:34]1[C:31]2[C:32](=[O:33])[N:28]([CH2:27][O:15][C:14]3[N:10]([C:7]4[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=4)[N:11]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:13]=3)[S:29](=[O:44])(=[O:43])[C:30]=2[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=1)([CH3:42])[CH3:41]

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 108825772-bromomethyl-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxideHCID 178526672HCID 178526672, compound

Product 1

HCID 189225824-isopropyl-6-methoxy-2-[1-(4-nitrophenyl)-3-trifluoromethylpyrazol-5-yl-oxymethyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxideYield 47.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 1-(4-nitrophenyl)-3-trifluoromethyl-5-hydroxypyrazole (450 mg; 1.65 mmol) and Cs2CO3 (269 mg; 0.825 mmol) in methanol (9 ml) was stirred at 20° C. for 4 hours. The solvent was concentrated in vacuo, and the residue was dried in vacuo overnight. To a solution of the above residue in 7 ml of DMF was added 2-bromomethyl-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (479 mg, 1.37 mmol) and the resulting mixture was stirred at room temperature (20° C.) for 3 hours and then poured into 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; 18-33% ethyl acetate in hexane) and recrystallized from methylene chloride/hexane to afford 350 mg (47%) of 4-isopropyl-6-methoxy-2-[1-(4-nitrophenyl)-3-trifluoromethylpyrazol-5-yl-oxymethyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (Formula I: R1 =4-NO2 --Ph; R2 =CF3 ; R3 =H; R4 =CH(CH3)2 ; R5 =6-OCH3) as a white solid, m.p. 185°-187° C.

Workup

  1. concentrationThe solvent was concentrated in vacuo
  2. customthe residue was dried in vacuo overnight
  3. stirringthe resulting mixture was stirred at room temperature (20° C.) for 3 hours
  4. extractionThe above mixture was extracted with ether (3×)
  5. dry with materialthe organic layer was dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (silica gel; 18-33% ethyl acetate in hexane)
  8. customrecrystallized from methylene chloride/hexane

Sources & evidence

ORD record
ord-efad2c1154f942f7b3a7607dc9c40868
Source dataset
uspto-grants-1998_05
Patent number
US05750550

Reaction notes

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