Ammonium Hydroxide → 2-(5-Isoxazolyl)benzenesulfonamide

HRID 1980775Notes

Reaction equation

HRID 1980775 reaction equation
[O:1]1[C:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[S:12](Cl)(=[O:14])=[O:13])=[CH:4][CH:3]=[N:2]1.[OH-].[NH4+:17]>O1CCCC1>[O:1]1[C:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[S:12]([NH2:17])(=[O:14])=[O:13])=[CH:4][CH:3]=[N:2]1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 134898112-(isoxazol-5-yl)benzene-1-sulfonyl chloride(WXC09362)

Product 1

HCID 134898132-(5-Isoxazolyl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 37 g of 2-(isoxazol-5-yl)benzenesulfonyl chloride, prepared in Example 4, in 200 ml of tetrahydrofuran, was cooled in an ice-water bath while about 40 ml of concentrated aqueous ammonium hydroxide was added slowly at 10° to 30° C. The resulting suspension was stirred at room temperature for 4 hours, then the solvent was evaporated under reduced pressure. The residue was stirred in 150 ml of water for 0.5 hour, then filtered. The crude, wet solid was dissolved in tetrahydrofuran and dried over sodium sulfate. The solid was recrystallized from 2-propanol to give 20 g of the title compound; m.p. 132°-135° C.

Workup

  1. additionwas added slowly at 10° to 30° C
  2. customthe solvent was evaporated under reduced pressure
  3. stirringThe residue was stirred in 150 ml of water for 0.5 hour
  4. filtrationfiltered
  5. dissolutionThe crude, wet solid was dissolved in tetrahydrofuran
  6. dry with materialdried over sodium sulfate
  7. customThe solid was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-846674876e3a418f8c09172163af26e1
Source dataset
uspto-grants-1985_04
Patent number
US04511392

Reaction notes

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