Benzoyl chloride → N-benzoyl-N'-(2-phenoxyphenyl)thiourea

HRID 1164516Notes

Reaction equation

HRID 1164516 reaction equation
[S-]C#N.[NH4+].C(Cl)(=O)C1C=CC=CC=1.[C:14]([N:22]=[C:23]=[S:24])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[O:25]([C:32]1[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=1[NH2:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CC(C)=O>[O:25]([C:32]1[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=1[NH:34][C:23]([NH:22][C:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[S:24])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 15666Ammonium thiocyanateHCID 68284Benzoyl isothiocyanateHCID 75899Benzenamine, 2-phenoxy-

Product 1

HCID 1488843N-benzoyl-N'-(2-phenoxyphenyl)thiourea

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution of ammonium thiocyanate (30.2 g) in anhydrous acetone (660 ml) was added dropwise benzoyl chloride (47.6 g) with stirring at 50° C. After refluxing for 1.5 hours, the mixture was cooled to ambient temperature. To the mixture containing benzoyl isothiocyanate was added dropwise a solution of 2-phenoxyaniline (47.6 g) in anhydrous acetone (300 ml). The reaction mixture was refluxed with stirring for 1.5 hours and then concentrated under reduced pressure to give crystals, which were washed twice with water and dried to give crystalline 1-(2-phenoxyphenyl)-3-benzoylthiourea.

Workup

  1. temperatureAfter refluxing for 1.5 hours
  2. temperaturethe mixture was cooled to ambient temperature
  3. temperatureThe reaction mixture was refluxed
  4. stirringwith stirring for 1.5 hours
  5. concentrationconcentrated under reduced pressure
  6. customto give crystals, which
  7. washwere washed twice with water
  8. customdried

Sources & evidence

ORD record
ord-ab736d83e5a04dc182afe110af8bf6be
Source dataset
uspto-grants-1983_01
Patent number
US04370340

Reaction notes

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