Ammonia → 2-(Thiophen-2-yl)ethane-1-sulfonamide

HRID 8609Notes

Reaction equation

HRID 8609 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][S:8](Cl)(=[O:10])=[O:9].[NH3:12].Cl>C1COCC1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][S:8]([NH2:12])(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 219837512-(Thiophen-2-yl)ethane-1-sulfonyl chloride

Product 1

HCID 637762602-(Thiophen-2-yl)ethane-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of crude 2-thiophen-2-yl-ethanesulfonyl chloride (25 g) in THF (400 ml) was treated with sat. aq. ammonia (60 ml) at 0° C. The mixture was stirred at rt for 16 h before it was neutralised with 25% aq. HCl (60 ml). Bulk of the THF was evaporated. The aq. solution was extracted twice with EA. The organic phase was washed with water and evaporated. The remaining oil was purified by chromatography on silica gel eluting with heptane:EA 1:1. The product was further purified by recrystallisation from diethyl ether/pentane to give 2-thiophen-2-yl-ethanesulfonic acid amide (8.46 g) as off-white crystals. 1H-NMR (300 MHz, CDCl3): 3.36–3.50(m, 4H), 4.54(s br, 2H), 6.89–6.92(m, 1H), 6.95(dd, J=3.5, 5.1, 1H), 7.20(dd, J=1.1, 5.0, 1H).

Workup

  1. customBulk of the THF was evaporated
  2. extractionThe aq. solution was extracted twice with EA
  3. washThe organic phase was washed with water
  4. customevaporated
  5. customThe remaining oil was purified by chromatography on silica gel eluting with heptane:EA 1:1
  6. customThe product was further purified by recrystallisation from diethyl ether/pentane

Sources & evidence

ORD record
ord-328b84d8da60496abda56ebd596892ca
Source dataset
uspto-grants-2006_08
Patent number
US07091201B2

Reaction notes

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