Propyl mercaptan → HCID 11393855, compound

HRID 430744Notes

Reaction equation

HRID 430744 reaction equation
[C:1]1([CH:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[S:8][CH2:9][C:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[C:18]([O:19]C)[C:13]=3[O:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(S)CC.CC(C)([O-])C.[K+].[Cl-].[NH4+]>CN(C=O)C>[C:21]1([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[S:8][CH2:9][C:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[C:18]([OH:19])[C:13]=3[O:12][CH:11]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 7848Propyl mercaptanHCID 25517Ammonium ChlorideHCID 11473887HCID 11473887, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 11393855HCID 11393855, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under argon atmosphere, 3-(diphenylmethylthiomethyl)-7-methoxybenzofuran (45 mg) was dissolved in DMF (3 ml) and the solution was stirred at room temperature. To this solution, n-propanethiol (0.20 ml) and potassium t-butoxide (47 mg) were added and the resulting solution was stirred at 100° C. After confirming vanishment of the materials, the reaction mixture was poured into saturated aqueous ammonium chloride solution (5 ml) and the resulting solution was extracted three times with ethyl acetate (10 ml). After combining the organic layers, the resultant was washed with saturated brine and dried over sodium sulfate. After removing the sodium sulfate by filtration, the solvent was removed under reduced pressure and the residue was purified by column chromatography (solvent: hexane/ethyl acetate=5/1-3/1) using silica gel to obtain the desired compound (26 mg, yield: 60%).

Workup

  1. stirringthe resulting solution was stirred at 100° C
  2. extractionthe resulting solution was extracted three times with ethyl acetate (10 ml)
  3. washthe resultant was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. customAfter removing the sodium sulfate
  6. filtrationby filtration
  7. customthe solvent was removed under reduced pressure
  8. customthe residue was purified by column chromatography (solvent: hexane/ethyl acetate=5/1-3/1)

Sources & evidence

ORD record
ord-04b6a8871f2b4be68b74e06d64b783ff
Source dataset
uspto-grants-2001_11
Patent number
US06323235B1

Reaction notes

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