Dimethylformamide → HCID 86752552, compound

HRID 1289882Notes

Reaction equation

HRID 1289882 reaction equation
Br[CH2:2][N:3]1[C:7](=[O:8])[C:6]2[C:9]([CH:15]([CH3:17])[CH3:16])=[CH:10][C:11]([O:13][CH3:14])=[CH:12][C:5]=2[S:4]1(=[O:19])=[O:18].[Cl:20][C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=1[N:28]1[C:32](=[O:33])[CH2:31][C:30]([C:34]#[N:35])=[N:29]1.[F-].[K+].CN(C=O)C>O>[CH:15]([C:9]1[C:6]2[C:7](=[O:8])[N:3]([CH2:2][O:33][C:32]3[N:28]([C:22]4[CH:23]=[CH:24][C:25]([Cl:27])=[CH:26][C:21]=4[Cl:20])[N:29]=[C:30]([C:34]#[N:35])[CH:31]=3)[S:4](=[O:19])(=[O:18])[C:5]=2[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=1)([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 522689Potassium FluorideHCID 108825772-bromomethyl-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxideHCID 189225661-(2,4-Dichlorophenyl)-4,5-dihydro-5-oxo-1H-pyrazole-3-carbonitrile

Product 1

HCID 86752552HCID 86752552, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-bromomethyl-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (410 mg, 1.18 mmol), 2,4-dihydro-2-(2,4-dichlorophenyl)-5-cyano-3H-pyrazol-3-one (300 mg, 1.18 mmol), KF (68.44 mg, 1.18 mmol) and DMF (20 mL) was stirred at room temperature overnight. The reaction mixture was diluted with water (100 mL) and was extracted with ether (3×50 mL). The ether extracts were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel eluting with 20% ethyl acetate/hexane to afford 310 mg of 4-isopropyl-6-methoxy-2-[1-(2, 4-dichlorophenyl)-3-cyanopyrazol-5-yl-oxymethyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (Formula I: R1 =2,4-Cl2 --Ph; R2 =CN; R3 =H; R4 =CH(CH3)2 ; R5 =6-OCH3), m.p. 183°-184° C.

Workup

  1. extractionwas extracted with ether (3×50 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography on silica gel eluting with 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-b16e06fce05544e6a08e759e01927232
Source dataset
uspto-grants-1998_05
Patent number
US05750550

Reaction notes

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