Acetic Acid → HCID 10017402, compound

HRID 1899687Notes

Reaction equation

HRID 1899687 reaction equation
[BH4-].[Na+].[C:3](O)(=O)[CH3:4].[H][H].[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([NH:19][C:20]2[O:24][N:23]=[C:22]([CH3:25])[C:21]=2[CH3:26])(=[O:18])=[O:17])=[CH:12][CH:11]=1.C(=O)(O)[O-].[Na+]>C1C=CC=CC=1>[CH2:3]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([NH:19][C:20]2[O:24][N:23]=[C:22]([CH3:25])[C:21]=2[CH3:26])(=[O:18])=[O:17])=[CH:12][CH:11]=1)[CH3:4]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 5344SulfisoxazoleHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 178418361HCID 178418361, compound

Product 1

HCID 10017402HCID 10017402, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Sodium borohydride (71 mg, 3.74 mmol) was added to a solution of acetic acid (740 mg, 12 mmol) in dry benzene (5 ml) with the temperature being kept at 20° C. When the evolution of hydrogen gas had ceased (ca. 5 min), 4-amino-N-(3,4-dimethyl-5-isoxazolyl)benzenesulfonamide (0.5 g, 1.87 mmol) was added in one lot and the reaction mixture was refluxed for 3 h. The reaction was cooled and shaken with saturated sodium bicarbonate solution. The organic layer was then washed with brine (2×20 ml), dried over magnesium sulfate and evaporated. the crude product was purified by column chromatography on silica gel using 1% methanol in chloroform as eluent to give 103 mg (19%) of a colorless oil. Further purification by HPLC gave a white solid, m.p. 123° C.

Workup

  1. custombeing kept at 20° C
  2. additionwas added in one lot
  3. temperaturethe reaction mixture was refluxed for 3 h
  4. temperatureThe reaction was cooled
  5. washThe organic layer was then washed with brine (2×20 ml)
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customthe crude product was purified by column chromatography on silica gel using 1% methanol in chloroform as eluent

Sources & evidence

ORD record
ord-04e90a1b6c6942d9bd55c780367b0c4a
Source dataset
uspto-grants-1996_11
Patent number
US05571821

Reaction notes

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