Benzoyl chloride → Benzoylthiourea

HRID 1111054Notes

Reaction equation

HRID 1111054 reaction equation
[S-:1][C:2]#[N:3].[NH4+:4].[C:5](Cl)(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CC(C)=O>[NH2:3][C:2](=[S:1])[NH:4][C:5](=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 15666Ammonium thiocyanate

Product 1

HCID 2735473BenzoylthioureaYield 54.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a two-liter-round-bottomed flask fitted with an overhead stirrer, addition funnel and a condenser was added 400 ml of acetone and 85.0 g (1.12 moles) of ammonium thiocyanate. To this solution was added 140.6 g (1.00 moles) of benzoyl chloride. The resultant slurry was heated at reflux for 15 minutes and then the heat was removed and 200 ml of concentrated ammonium hydroxide was added at a rate to maintain reflux. The reaction mixture was heated at reflux for an additional 15 minutes and then cooled to room temperature. This mixture was added to 6 liters of water, and the resulting precipitate was collected by filtration and washed with 2 liters of water, then air dried and recrystallized from 1.5 liters of ethanol to give 98.5 g of the desired product as a white solid, mp 170°-171° C.

Workup

  1. customTo a two-liter-round-bottomed flask fitted with an overhead stirrer, addition funnel and a condenser
  2. temperatureThe resultant slurry was heated
  3. temperatureat reflux for 15 minutes
  4. customthe heat was removed
  5. addition200 ml of concentrated ammonium hydroxide was added at a rate
  6. temperatureto maintain
  7. temperaturereflux
  8. temperatureThe reaction mixture was heated
  9. temperatureat reflux for an additional 15 minutes
  10. additionThis mixture was added to 6 liters of water
  11. filtrationthe resulting precipitate was collected by filtration
  12. washwashed with 2 liters of water
  13. customair dried
  14. customrecrystallized from 1.5 liters of ethanol

Sources & evidence

ORD record
ord-190067b41a6640debe3d53312ae820e8
Source dataset
uspto-grants-1990_12
Patent number
US04977189

Reaction notes

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