Ammonia → 2-(Chloromethyl)benzenesulfonamide

HRID 279753Notes

Reaction equation

HRID 279753 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°.

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-3b479579d7ab4b88bbf74d23a6c1b360
Source dataset
uspto-grants-1986_05
Patent number
US04586952

Reaction notes

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