Water → 2-(Methylthio)-6-phenylbenzenesulfonamide

HRID 34870Notes

Reaction equation

HRID 34870 reaction equation
O.CC([NH:6][S:7]([C:10]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:14][CH:13]=[CH:12][C:11]=1[S:22][CH3:23])(=[O:9])=[O:8])(C)C>FC(F)(F)C(O)=O>[CH3:23][S:22][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]=1[S:7]([NH2:6])(=[O:9])=[O:8]

Participants

4

Reactant 2

HCID 962WaterHCID 13670365N-(1,1-dimethylethyl)-2-(methylthio)-6-phenylbenzenesulfonamide

Product 1

HCID 136703672-(Methylthio)-6-phenylbenzenesulfonamideYield 77.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

In a mixture of 75 ml trifluoroacetic acid plus 2 ml water was dissolved 10 g (0.030 mol) of N-(1,1-dimethylethyl)-2-(methylthio)-6-phenylbenzenesulfonamide and heated to 85°. After 15 minutes the mixture was cooled and evaporated, then diluted with water and extracted with methylene chloride. The methylene chloride was washed with saturated sodium bicarbonate solution, dried (MgSO4), evaporated in vacuo and crystallized from ether/hexanes to afford 6.5 g of the title compound, m.p. 167°-168°.

Workup

  1. temperatureheated to 85°
  2. temperatureAfter 15 minutes the mixture was cooled
  3. customevaporated
  4. additiondiluted with water
  5. extractionextracted with methylene chloride
  6. washThe methylene chloride was washed with saturated sodium bicarbonate solution
  7. dry with materialdried (MgSO4)
  8. customevaporated in vacuo
  9. customcrystallized from ether/hexanes

Sources & evidence

ORD record
ord-16cb48a43d084980a12d76d857bb8ab1
Source dataset
uspto-grants-1988_08
Patent number
US04764204

Reaction notes

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