Triethylsilane → HCID 57718307, compound

HRID 1984579Notes

Reaction equation

HRID 1984579 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 ×3 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%. 1H NMR 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 ×3
  7. washthe organic solution washed with water, dried MgSO4
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-dbffb18d526144a599086423da6e7e4f
Source dataset
uspto-grants-2009_06
Patent number
US07544702B2

Reaction notes

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