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

HRID 1252354Notes

Reaction equation

HRID 1252354 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-7e224f623a854442a8b666c41257abe6
Source dataset
uspto-grants-1988_05
Patent number
US04743290

Reaction notes

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