Acetone → HCID 22908154, compound

HRID 1379803Notes

Reaction equation

HRID 1379803 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1)#[N:2].[S-:12][C:13]#[N:14].[NH4+:15].[CH3:16][C:17]([CH3:19])=O>>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH:14][C:13]([NH:15][CH2:16][CH2:17][C:19]2[CH:10]=[CH:11][CH:3]=[CH:4][CH:5]=2)=[S:12])=[O:8])=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 3

HCID 180AcetoneHCID 15666Ammonium thiocyanateHCID 801724-Cyanobenzoyl chloride

Product 1

HCID 22908154HCID 22908154, compound

Procedure

4-Cyanobenzoyl chloride (12.5 g) was added to a solution of ammonium thiocyanate (5.8 g) in acetone (125 ml) at room temperature, followed by heating under reflux for 15 minutes. The reaction mixture was ice-cooled, and after removal of the insoluble substance by filtration, the filtrate was evaporated under reduced pressure. To the resulting residue were added toluene (125 ml) and 2-phenylethylamine (10.4 g) successively, followed by stirring for 2 hours. The reaction mixture was concentrated under reduced pressure, and the resulting crude crystals were washed with ethyl acetate to give 1-(4-cyanobenzoyl)-3-(2-phenylethyl)thiourea (14.1 g).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 15 minutes
  3. temperaturecooled
  4. customafter removal of the insoluble substance
  5. filtrationby filtration
  6. customthe filtrate was evaporated under reduced pressure
  7. additionTo the resulting residue were added toluene (125 ml) and 2-phenylethylamine (10.4 g) successively
  8. concentrationThe reaction mixture was concentrated under reduced pressure
  9. washthe resulting crude crystals were washed with ethyl acetate

Sources & evidence

ORD record
ord-29b353c6eea34bf58da207c8edb04504
Source dataset
uspto-grants-1997_09
Patent number
US05672712

Reaction notes

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