Ammonia → 2-(1-Chloroethyl)benzenesulfonamide

HRID 4141Notes

Reaction equation

HRID 4141 reaction equation
[NH3:1].[Cl:2][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11](Cl)(=[O:13])=[O:12])[CH3:4]>O1CCCC1>[Cl:2][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([NH2:1])(=[O:13])=[O:12])[CH3:4]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 133646252-(1-Chloroethyl)benzenesulfonyl chloride

Product 1

HCID 133646282-(1-Chloroethyl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ammonia (1.2 ml) in tetrahydrofuran (100 ml) at -70° was contacted rapidly with a solution of 2-(1-chloroethyl)benzenesulfonyl chloride (4.32 g, 18.1 mmol) in tetrahydrofuran (50 ml). The stirred mixture was allowed to warm to 0° and volatiles were removed under reduced pressure. The residue was taken up in ethyl acetate and washed with a small volume of water and brine. The dried (MgSO4) solution was evaporated to give 4.7 g of off white solid which was recrystallized from chloroform to give 3.13 g, m.p. 121°-122°. 1H nmr δ(CD3)2COTMS 8.25-7.30 (m), 6.93 (brds), 6.25 (q, J=7 Hz), 3.17 (s), 1.98 (d, J=7 Hz).

Workup

  1. customat -70°
  2. temperatureto warm to 0°
  3. customvolatiles were removed under reduced pressure
  4. washwashed with a small volume of water and brine
  5. dry with materialThe dried (MgSO4) solution
  6. customwas evaporated
  7. customto give 4.7 g of off white solid which
  8. customwas recrystallized from chloroform
  9. customto give 3.13 g, m.p. 121°-122°

Sources & evidence

ORD record
ord-81369e951b824169a8227c813fb01c19
Source dataset
uspto-grants-1988_02
Patent number
US04723990

Reaction notes

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