Potassium thiocyanate → 4-(4-Benzamidobutyl)-5-methylimidazole-2-thione

HRID 261619Notes

Reaction equation

HRID 261619 reaction equation
Cl.[NH2:2][CH:3]([CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:4](=O)[CH3:5].[S-:20][C:21]#[N:22].[K+]>O>[C:12]([NH:11][CH2:10][CH2:9][CH2:8][CH2:7][C:3]1[C:4]([CH3:5])=[N:22][C:21](=[S:20])[N:2]=1)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 516872Potassium thiocyanateHCID 203945683-Amino-7-benzamidoheptan-2-one hydrochloride

Product 1

HCID 203945574-(4-Benzamidobutyl)-5-methylimidazole-2-thioneYield 25.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3-amino-7-benzamidoheptan-2-one hydrochloride (16.39 g, 0.0576 mol) and potassium thiocyanate (7.30 g, 0.0755 mol, excess) in water was heated under reflux for 20 hours. The aquesus phase was decanted off and the organic phase was washed with water, and recrystallised from acetonitrile to give 4-(4-benzamidobutyl)-5-methylimidazole-2-thione (4.18 g, 25%) m.p. 180°-184°.

Workup

  1. temperatureunder reflux for 20 hours
  2. customThe aquesus phase was decanted off
  3. washthe organic phase was washed with water
  4. customrecrystallised from acetonitrile

Sources & evidence

ORD record
ord-d1526fc277ce41089995dc0eceed56f5
Source dataset
uspto-grants-1979_08
Patent number
US04166184

Reaction notes

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