Ammonia → 2-(Chloromethyl)benzenesulfonamide

HRID 1153864Notes

Reaction equation

HRID 1153864 reaction equation
[NH3:1].[Cl:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](Cl)(=[O:12])=[O:11]>O1CCCC1>[Cl:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH2:1])(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 124047572-(Chloromethyl)benzene-1-sulfonyl chloride

Product 1

HCID 133646272-(Chloromethyl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ammonia (5.2 ml) in tetrahydrofuran (250 ml) at -70° was contacted rapidly with a solution of 2-(chloromethyl)benzenesulfonyl chloride (21.8 g) in tetrahydrofuran (125 ml). The stirred mixture was allowed to warm to 0° and volatiles were removed under vacuum. The residue was contacted with ethyl acetate and a small volume of water. The organic layer was dried (MgSO4) and evaporated to give 19.8 g of white solid, m.p. 156°-157.5°. Recrystallization from toluene/ethyl acetate gave a sample with m.p. 157°-160°. 1H nmr δ(CD3)2COTMS 8.16-7.35 (m), 6.75 brds), 5.20 (s), 3.08 (s).

Workup

  1. customat -70°
  2. temperatureto warm to 0°
  3. customvolatiles were removed under vacuum
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-f2c23c47ee5140e6851aa0af9a9221a7
Source dataset
uspto-grants-1984_12
Patent number
US04486589

Reaction notes

Loading…