Benzyl Isothiocyanate → (cyclohexylphenylamino)-N-benzylthiocarboxamide

HRID 890507Notes

Reaction equation

HRID 890507 reaction equation
[CH:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:14]([N:21]=[C:22]=[S:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(#N)C.CN(C)C1C=CN=CC=1>[CH:8]1([N:7]([C:22]([NH:21][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[S:23])[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 2346Benzyl IsothiocyanateHCID 74567N-Cyclohexylaniline

Product 1

HCID 21304109(cyclohexylphenylamino)-N-benzylthiocarboxamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of N-cyclohexylaniline (0.1 ml, 0.57 mmol) in acetonitrile (4 ml) was added a catalytic amount of 4-(dimethylamino)pyridine (5 mg, 0.04 mmol). To this mixture was added benzyl isothiocyanate (0.11 ml, 0.83 mmol) dropwise, and the mixture was stirred at room temperature for 16 hours. The solvent was removed under reduced pressure, and the residue purified on preparative silica gel plates, developing with 20% ethyl acetate/hexanes, to furnish (N-cyclohexyl-N-phenylamino)-N-benzylthiocarboxamide as a white solid, (M+1)=324.8.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue purified on preparative silica gel plates

Sources & evidence

ORD record
ord-e3a194a221d74504b4050a9a527a6609
Source dataset
uspto-grants-2006_02
Patent number
US06995285B2

Reaction notes

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