4-Fluorobenzonitrile → 4-(Thiomorpholin-4-yl)benzonitrile
Reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[NH:10]1[CH2:15][CH2:14][S:13][CH2:12][CH2:11]1>C(#N)C>[S:13]1[CH2:14][CH2:15][N:10]([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)[CH2:11][CH2:12]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
4-fluorobenzonitrile (500 mg, 4.13 mmol) and thiomorpholine (1.18 ml, 12.4 mmol) was dissolved in acetonitrile (2 ml) and stirred at 100° C. for 40 hours. The reaction was cooled, evaporated and purified by flash chromatography using pet.ether/EtOAc (4:1) as eluent to give 450 mg (53%) of the title compound as pale solids.
Workup
- temperatureThe reaction was cooled
- customevaporated
- custompurified by flash chromatography
Sources & evidence
- ORD record
- ord-e5166f7fe0984a36b8c559992959d2f0
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08415333B2
Reaction notes
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