HCID 13424188, compound → HCID 13424189, compound

HRID 1981272Notes

Reaction equation

HRID 1981272 reaction equation
C([NH:5][S:6]([C:9]1[C:14]2[S:15][C:16]([CH3:19])([CH3:18])[CH2:17][C:13]=2[CH:12]=[CH:11][CH:10]=1)(=[O:8])=[O:7])(C)(C)C>FC(F)(F)C(O)=O>[CH3:18][C:16]1([CH3:19])[S:15][C:14]2[C:9]([S:6]([NH2:5])(=[O:8])=[O:7])=[CH:10][CH:11]=[CH:12][C:13]=2[CH2:17]1

Participants

3

Reactant 1

HCID 13424188HCID 13424188, compound

Product 1

HCID 13424189HCID 13424189, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 17.2 g of N-t-butyl-2,3-dihydro-2,2-dimethyl-7-benzo[b]thiophenesulfonamide (Example 13) in 100 ml of trifluoroacetic acid was stirred at 20° C. for 16 hours. The solution was concentrated in vacuo, 100 ml of fresh trifluoroacetic acid was added and the mixture stirred at 20° C. for four more hours. After concentrating the solution in vacuo, the residue was dissolved in methylene chloride and the solution was washed with saturated aqueous sodium bicarbonate followed by brine, then dried over magnesium sulfate and concentrated in vacuo. The solid residue was slurried in 50% ether in hexane for several minutes then filtered to yield 8.4 g of the title compound; m.p. 102°-104° C.

Workup

  1. concentrationThe solution was concentrated in vacuo, 100 ml of fresh trifluoroacetic acid
  2. additionwas added
  3. concentrationAfter concentrating the solution in vacuo
  4. dissolutionthe residue was dissolved in methylene chloride
  5. washthe solution was washed with saturated aqueous sodium bicarbonate
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. waitThe solid residue was slurried in 50% ether in hexane for several minutes
  9. filtrationthen filtered

Sources & evidence

ORD record
ord-044aec0cc968424aac1ab0f4b75d9a4a
Source dataset
uspto-grants-1985_04
Patent number
US04514211

Reaction notes

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