5-Chloro-2-methylaniline → 1-(5-Chloro-2-methylphenyl)-2-thiourea

HRID 1698865Notes

Reaction equation

HRID 1698865 reaction equation
C(Cl)(=O)C1C=CC=CC=1.[S-:10][C:11]#[N:12].[NH4+].[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([CH3:22])=[C:19]([CH:21]=1)[NH2:20]>CC(C)=O.ClCCl>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([CH3:22])=[C:19]([NH:20][C:11]([NH2:12])=[S:10])[CH:21]=1

Participants

6

Reactant 3

HCID 72605-Chloro-2-methylanilineHCID 7412Benzoyl chlorideHCID 15666Ammonium thiocyanate

Product 1

HCID 27577031-(5-Chloro-2-methylphenyl)-2-thiourea

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

8.9 ml of benzoyl chloride are added to a solution of 5.9 g of ammonium thiocyanate in 130 ml of anhydrous acetone. The reaction mixture is heated under reflux for 15 minutes and then after cooling, 10 g of 5-chloro-2-methylaniline are added. The reaction mixture is heated under reflux for 2 hours and the acetone is removed by distillation under vacuum. The residue obtained is taken up in dichloromethane. The mixture is washed with water, dried over sodium sulphate and evaporated under vacuum. The expected product is obtained in the form of an oil with a quantitative yield.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for 15 minutes
  3. temperatureafter cooling
  4. temperatureThe reaction mixture is heated
  5. temperatureunder reflux for 2 hours
  6. customthe acetone is removed by distillation under vacuum
  7. customThe residue obtained
  8. washThe mixture is washed with water
  9. dry with materialdried over sodium sulphate
  10. customevaporated under vacuum

Sources & evidence

ORD record
ord-9f6de110b55a46199ee54056e0649064
Source dataset
uspto-grants-2002_02
Patent number
US06344470B1

Reaction notes

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