3-Cyano-N-(1,1-dimethylethyl)thiophene-2-sulfonamide → 3-Cyanothiophene-2-sulfonamide

HRID 2352467Notes

Reaction equation

HRID 2352467 reaction equation
[C:1]([C:3]1[CH:7]=[CH:6][S:5][C:4]=1[S:8]([NH:11]C(C)(C)C)(=[O:10])=[O:9])#[N:2]>FC(F)(F)C(O)=O>[C:1]([C:3]1[CH:7]=[CH:6][S:5][C:4]=1[S:8]([NH2:11])(=[O:10])=[O:9])#[N:2]

Participants

3

Reactant 1

HCID 142549393-Cyano-N-(1,1-dimethylethyl)thiophene-2-sulfonamide

Product 1

HCID 142549403-Cyanothiophene-2-sulfonamideYield 83.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Ten grams of 3-cyano-N-(1,1-dimethylethyl)thiophene-2-sulfonamide was dissolved in 500 mL of trifluoroacetic acid and stirred overnight at room temperature. After removal of the solvent by evaporation, the residue was dissolved in ethyl acetate and washed with four portions of 100 mL of water followed by saturated sodium chloride. After drying over magnesium sulfate, the solvent was evaporated in vacuo to yield 6.42 g of white solid, m.p. 152°-155°. It showed peaks by Nuclear Magnetic Resonance consistent for the desired structure.

Workup

  1. customAfter removal of the solvent
  2. customby evaporation
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with four portions of 100 mL of water
  5. dry with materialAfter drying over magnesium sulfate
  6. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-bfcf53eff5094ae4b08df615d47153a1
Source dataset
uspto-grants-1989_10
Patent number
US04877440

Reaction notes

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