Triethylsilane → HCID 57718307, compound

HRID 1366827Notes

Reaction equation

HRID 1366827 reaction equation
[CH2:1]([NH:3][S:4]([C:7]1[CH:12]=[CH:11][C:10]([S:13]CC2C=CC(OC)=CC=2)=[CH:9][CH:8]=1)(=[O:6])=[O:5])[CH3:2].C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[CH2:1]([NH:3][S:4]([C:7]1[CH:12]=[CH:11][C:10]([SH:13])=[CH:9][CH:8]=1)(=[O:5])=[O:6])[CH3:2]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 11537368HCID 11537368, compound

Product 1

HCID 57718307HCID 57718307, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
80 °C

Procedure

To N-ethyl-4-(4-methoxy-benzylsulfanyl)-benzenesulfonamide 5.95 g was added trifluoroacetic acid 60 ml containing triethyl silane 3 ml and the mixture heated at 80° C. for 2 h. The reaction mixture was cooled and evaporated in vacuo. The residue was taken up in ethyl acetate and evaporated in vacuo ×2. The residue was then taken up in ethyl acetate and extracted with 2M sodium hydroxide 3×30 ml and the combined aqueous solution washed with ethyl acetate (×1). The aqueous solution was then acidified with conc. hydrochloric acid and extracted with dichloromethane X3 and the organic solution washed with water, dried MgSO4 and evaporated in vacuo to give N-ethyl-4-mercapto-benzenesulfonamide, as a pale yellow oil, 3.05 g 79%. 1HNMR 7.72 (2H, d), 7.34 (2H, d), 4.65 (1H, bs), 3.70 (1H, s), 2.99 (2H, q), 1.11 (3H, t).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customevaporated in vacuo
  3. customevaporated in vacuo ×2
  4. extractionextracted with 2M sodium hydroxide 3×30 ml
  5. washthe combined aqueous solution washed with ethyl acetate (×1)
  6. extractionextracted with dichloromethane X3
  7. washthe organic solution washed with water, dried MgSO4
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-5b532205a19541f288cd4ad9690828a3
Source dataset
uspto-grants-2011_02
Patent number
US07893077B2

Reaction notes

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