Water → HCID 19931990, compound

HRID 21606Notes

Reaction equation

HRID 21606 reaction equation
[BH4-].[Na+].[CH2:3]([N:5]([CH2:26][CH3:27])[C:6]([N:8]1[CH:12]=[C:11]([CH:13]=[O:14])[C:10]([S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:19]=2[CH3:25])(=[O:17])=[O:16])=[N:9]1)=[O:7])[CH3:4].O>CO>[CH2:26]([N:5]([CH2:3][CH3:4])[C:6]([N:8]1[CH:12]=[C:11]([CH2:13][OH:14])[C:10]([S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:19]=2[CH3:25])(=[O:17])=[O:16])=[N:9]1)=[O:7])[CH3:27]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 199319281-(Diethylcarbamoyl)-3-(2-methyl-3-chlorophenylsulfonyl)-4-formylpyrazole

Product 1

HCID 19931990HCID 19931990, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

11 mg of sodium borohydride were added at 0° C. to a solution of 112 mg of 1-(diethylcarbamoyl)-3-(2-methyl-3-chlorophenylsulfonyl)-4-formylpyrazole [prepared as described in Example 9(3)] in 3.5 ml of methanol, and the resulting mixture was stirred for 30 minutes. At the end of this time, the reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated by evaporation under reduced pressure. The concentrate was purified by column chromatography through silica gel, eluted with a 5:1 by volume mixture of hexane and ethyl acetate, to afford 114 mg (a quantitative yield) of the title compound as an oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated by evaporation under reduced pressure
  5. customThe concentrate was purified by column chromatography through silica gel
  6. washeluted with a 5:1 by volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-f8abc9b5745740e9b329aee1eeb3172f
Source dataset
uspto-grants-1995_06
Patent number
US05424279

Reaction notes

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