Benzyl Isothiocyanate → 1-Benzyl-3-phenyl-2-thiourea

HRID 1761458Notes

Reaction equation

HRID 1761458 reaction equation
[CH2:1]([N:8]=[C:9]=[S:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1(C)C=CC=CC=1>[C:12]1([NH:11][C:9]([NH:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[S:10])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 2346Benzyl IsothiocyanateHCID 6115Aniline

Product 1

HCID 6683001-Benzyl-3-phenyl-2-thiourea

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 74.6 g (0.5 mol) of benzylisothiocyanate in 500 mL toluene was added dropwise 46.6 g (0.5 mol) of aniline. The solution was refluxed 18 hours. After cooling, the reaction mixture was concentrated under reduced pressure. The residue was recrystallized from an appropriate solvent to yield N-phenyl-N'-benzylthiourea. Isothiocyanates which are not commercially available may be prepared from aliphatic or aryl primary amines by the following methods: Kurita and Iwakura, Org. Synth. 59, 195; Jochims, Chem. Ber. 101, 1746 (1968); or Castro, Pena, Santos, and Vega, J. Org. Chem. 49, 863 (1984).

Workup

  1. temperatureThe solution was refluxed 18 hours
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. customThe residue was recrystallized from an appropriate solvent

Sources & evidence

ORD record
ord-5a59bd43d34c4964becda4a4e2a76a0d
Source dataset
uspto-grants-1989_05
Patent number
US04826860

Reaction notes

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