Benzoyl chloride → Thiourea, [3-(dimethylamino)-2-methylphenyl]-

HRID 24981Notes

Reaction equation

HRID 24981 reaction equation
[CH3:1][N:2]([CH3:11])[C:3]1[C:4]([CH3:10])=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].[C:12]([S-:14])#[N:13].[K+].C(Cl)(=O)C1C=CC=CC=1.[OH-].[K+]>C(O)C.O.CC(C)=O>[CH3:1][N:2]([CH3:11])[C:3]1[C:4]([CH3:10])=[C:5]([NH:6][C:12]([NH2:13])=[S:14])[CH:7]=[CH:8][CH:9]=1

Participants

8

Reactant 4

HCID 7412Benzoyl chlorideHCID 14797Potassium HydroxideHCID 516872Potassium thiocyanateHCID 111373411,3-Benzenediamine,N,N,2-trimethyl-(9CI)

Product 1

HCID 10856728Thiourea, [3-(dimethylamino)-2-methylphenyl]-Yield 91.3%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 702EthanolSolvent2×HCID 962WaterSolvent2×

Procedure

57 g of 3-dimethylamino-2-methyl-aniline, 1.15 liters of acetone, 36.6 g of KSCN and 43.8 ml of benzoylchloride are refluxed together for 3 hours. After cooling to ambient temperature the reaction mixture is poured onto 2.4 kg of crushed ice. The precipitate obtained is heated to 60° C. for 2 hours together with 85 g of KOH, 85 ml of water and 255 ml of ethanol. After the addition of 850 ml of water the ethanol is distilled off under reduced pressure. After the resulting precipitate has been worked up, 72 g of N-(3-dimethylamino-2-methylphenyl)-thiourea are obtained.

Workup

  1. customThe precipitate obtained
  2. distillationis distilled off under reduced pressure

Sources & evidence

ORD record
ord-4af9c31168e94a3c9a00a55a1e5628d3
Source dataset
uspto-grants-2005_02
Patent number
US06858594B2

Reaction notes

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