Ammonia → 2-Chloro-4-(2-oxo-propyl)-benzenesulfonamide

HRID 908149Notes

Reaction equation

HRID 908149 reaction equation
[NH3:1].[Cl:2][C:3]1[CH:8]=[C:7]([CH2:9][C:10](=[O:12])[CH3:11])[CH:6]=[CH:5][C:4]=1[S:13](Cl)(=[O:15])=[O:14]>O1CCCC1>[Cl:2][C:3]1[CH:8]=[C:7]([CH2:9][C:10](=[O:12])[CH3:11])[CH:6]=[CH:5][C:4]=1[S:13]([NH2:1])(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 859968242-Chloro-4-(2-oxo-propyl)-benzenesulfonyl chloride

Product 1

HCID 673917572-Chloro-4-(2-oxo-propyl)-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Aqueous ammonia solution (5 ml) is added to a stirred solution of the crude sulfonyl chloride (23b) (0.70 g, 2.62 mmol) in tetrahydrofuran (100 ml) at 0° C. After 2 hours the reaction mixture is concentrated in vacuo. The residue is diluted with water (100 ml) and extracted with ethyl acetate (100 ml). The organic extract is dried (MgSO4) and the solvent removed to give an oil. Purification by chromatography on silica, eluting with ethyl acetate, affords the title compound (0.154 g).

Workup

  1. concentrationAfter 2 hours the reaction mixture is concentrated in vacuo
  2. additionThe residue is diluted with water (100 ml)
  3. extractionextracted with ethyl acetate (100 ml)
  4. extractionThe organic extract
  5. dry with materialis dried (MgSO4)
  6. customthe solvent removed
  7. customto give an oil
  8. customPurification by chromatography on silica
  9. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-5f5ec66511394ae7a3c3daed106f91d4
Source dataset
uspto-grants-2011_09
Patent number
US08017608B2

Reaction notes

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