4-Fluorobenzonitrile → 4-(Thiomorpholin-4-yl)benzonitrile

HRID 1961431Notes

Reaction equation

HRID 1961431 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]1

Participants

4

Reactant 2

HCID 145174-FluorobenzonitrileHCID 67164Thiomorpholine

Product 1

HCID 232929824-(Thiomorpholin-4-yl)benzonitrileYield 53.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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

  1. temperatureThe reaction was cooled
  2. customevaporated
  3. 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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