Benzyl mercaptan → 4-(Benzylthio)-2-(trifluoromethyl)pyridine
Reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:3]=1.N12CCCN=C1CCCCC2.[C:23]1([CH2:29][SH:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C)C=O>[CH2:29]([S:30][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:3]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1Participants
Conditions
- Temperature
- 100 °C
Procedure
4-Chloro-2-(trifluoromethyl)pyridine (141 μl, 1.102 mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (199 μl, 1.322 mmol), and phenylmethanethiol (129 μl, 1.102 mmol) were dissolved in dry dimethylformamide (2 mL). The reaction mixture was heated at 100° C. in a microwave for 30 minutes, then partitioned between ether (25 mL) and water (25 mL). The aqueous layer was extracted with ether (2×25 mL) and the combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo to give a pale yellow oil. The crude product was purified by chromatography on silica gel (gradient: 0-30% ethyl acetate in isohexane) to afford 4-(benzylthio)-2-(trifluoromethyl)pyridine (224 mg) as a colourless oil. LCMS (Method F, ES-API): RT 2.79 min, m+H=270.1.
Workup
- custompartitioned between ether (25 mL) and water (25 mL)
- extractionThe aqueous layer was extracted with ether (2×25 mL)
- dry with materialthe combined organic layers were dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customto give a pale yellow oil
- customThe crude product was purified by chromatography on silica gel (gradient: 0-30% ethyl acetate in isohexane)
Sources & evidence
- ORD record
- ord-e0ca3873eff24a739d20d876cc7fa909
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08859774B2
Reaction notes
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