Ammonia → Benzeneethanesulfonamide

HRID 8592Notes

Reaction equation

HRID 8592 reaction equation
[C:1]1([CH2:7][CH2:8][S:9](Cl)(=[O:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH3:13].Cl>C1COCC1>[C:1]1([CH2:7][CH2:8][S:9]([NH2:13])(=[O:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 27603742-Phenylethane-1-sulfonyl chloride

Product 1

HCID 204808Benzeneethanesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-phenylethanesulfonyl chloride (40.94 g) in THF (250 ml) was cooled to −20° C. before it was treated with sat. aq. ammonia (50 ml). The brown suspension was stirred at rt for 16 h. The mixture was neutralised with aq. HCl and the organic solvent was evaporated. The remaining suspension was diluted with water and extracted four times with EA. The organic layers were combined and evaporated to give 2-phenyl-ethanesulfonic acid amide (33.06 g) as orange solid. 1H-NMR(300 MHz, CDCl3): 3.15–3.21(m, 2H), 3.38–3.45(m, 2H), 4.59(s br, 2H), 7.21–7.37(m, 5H).

Workup

  1. customthe organic solvent was evaporated
  2. additionThe remaining suspension was diluted with water
  3. extractionextracted four times with EA
  4. customevaporated

Sources & evidence

ORD record
ord-aefda4e42cde42d1b7ffd52f52e1272a
Source dataset
uspto-grants-2006_08
Patent number
US07091201B2

Reaction notes

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