Water → 2-Chloro-6-phenylbenzenesulfonamide

HRID 236230Notes

Reaction equation

HRID 236230 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:3]=1[S:14]([NH:17]C(C)(C)C)(=[O:16])=[O:15].O>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:3]=1[S:14]([NH2:17])(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 962WaterHCID 138523512-Chloro-N-(1,1-dimethylethyl)-6-phenylbenzenesulfonamide

Product 1

HCID 138523522-Chloro-6-phenylbenzenesulfonamideYield 83.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 2-chloro-N-(1,1-dimethylethyl)-6-phenylbenzenesulfonamide (23 g, 0.071 mol) in a mixture of 120 ml trifluoroacetic acid (TFA) plus 4 ml water was heated to reflux for 2 hours. The TFA was evaporated in vacuo and the residue partitioned between methylene chloride and water. The organic layer was dried (MgSO4), evaporated, and the residue crystallized from ether/methylene chloride to afford 15.9 g of crystalline solid in two crops, m.p. 185°-87°. NMR (90 MHZ, CDCl3) 6.45 (s, br, NH2). 7.3-7.7 (m, 8H) ppm.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. customThe TFA was evaporated in vacuo
  4. customthe residue partitioned between methylene chloride and water
  5. dry with materialThe organic layer was dried (MgSO4)
  6. customevaporated
  7. customthe residue crystallized from ether/methylene chloride

Sources & evidence

ORD record
ord-55d38d434a644a75b9e768c1bf1f5464
Source dataset
uspto-grants-1987_02
Patent number
US04643761

Reaction notes

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