Benzyl mercaptan → 4-(benzylthio)benzonitrile

HRID 911268Notes

Reaction equation

HRID 911268 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH2:10]([SH:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1C(=O)CCC1>[CH2:10]([S:17][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 10796Cesium carbonateHCID 145174-Fluorobenzonitrile

Product 1

HCID 8525724-(benzylthio)benzonitrileYield 31%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

Mix under argon atmosphere 4-fluorobenzonitrile (1.21 g, 10 mmol), benzyl mercaptan (1.86 g, 15 mmol), and cesium carbonate (6.5 g, 20 mmol) in anhydrous NMP (20 mL). Degas the flask and fill with argon. Heat at 120° C. for 3 h. Cool to ambient temperature, dilute with EtOAc, filter and wash with 1N aqueous HCl. Separate the organic layer, dry over Na2SO4 and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (1:0 and 9:1) to obtain the desired intermediate (689 mg, 31%). GC-MS m/z: 225 (M+).

Workup

  1. customDegas the flask
  2. temperatureCool to ambient temperature
  3. additiondilute with EtOAc
  4. filtrationfilter
  5. washwash with 1N aqueous HCl
  6. customSeparate the organic layer
  7. dry with materialdry over Na2SO4
  8. concentrationconcentrate in vacuo
  9. customPurify by chromatography on silica gel eluting with hexane/EtOAc (1:0 and 9:1)

Sources & evidence

ORD record
ord-14c9473e05974c70b5ef43909ddb0303
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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