Benzyl mercaptan → Ethyl 6-(benzylsulfanyl)-1-cyclohexene-1-carboxylate

HRID 1793197Notes

Reaction equation

HRID 1793197 reaction equation
FC1C=C(F)C=CC=1N[S:10]([CH:13]1[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][CH2:16][CH2:15][CH2:14]1)(=O)=O.[C:24]1([CH2:30]S)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C1CCN2C(=NCCC2)CC1>CN(C)C=O.C(OCC)(=O)C>[CH2:30]([S:10][CH:13]1[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][CH2:16][CH2:15][CH2:14]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 7509Benzyl mercaptanHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 9928140ethyl 6-[N-(2,4-difluorophenyl)sulfamoyl]-1-cyclohexene-1-carboxylate

Product 1

HCID 22026126Ethyl 6-(benzylsulfanyl)-1-cyclohexene-1-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 6-[N-(2,4-difluorophenyl)sulfamoyl]-1-cyclohexene-1-carboxylate (1 g, synthesized according to the method disclosed in JP-A-10-056492) and phenylmethanethiol (719 mg) in N,N-dimethylformamide (20 ml) was added dropwise under ice-cooling 1,8-diazabicyclo[5,4,0]-7-undecene (441 mg) and the mixture was stirred at room temperature for 18 h. The reaction mixture was diluted with ethyl acetate (100 ml), washed with water (70 ml×2) and saturated brine (70 ml), and dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained residue was purified by flash silica gel column chromatography (eluent: toluene) to give ethyl 6-(benzylsulfanyl)-1-cyclohexene-1-carboxylate (673 mg) as a colorless oil. 1H-NMR(CDCl3)δ: 1.27 (3H, t, J=7.0 Hz), 1.55–2.36 (6H, m), 3.76 (1H, m), 3.86 (2H, s), 4.19 (2H, q, J=7.0 Hz), 6.95 (1H, t, J=4.0 Hz), 7.22–7.39 (5H, m).

Workup

  1. additionwas added dropwise under ice-
  2. washwashed with water (70 ml×2) and saturated brine (70 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated
  5. customthe obtained residue was purified by flash silica gel column chromatography (eluent: toluene)

Sources & evidence

ORD record
ord-a9dd66b024284e8ba5081694ebe1d0d1
Source dataset
uspto-grants-2006_07
Patent number
US07078540B1

Reaction notes

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