Acetone → n-[(2,6-dimethylphenyl)carbamothioyl]benzamide

HRID 2398829Notes

Reaction equation

HRID 2398829 reaction equation
[S-:1][C:2]#[N:3].[NH4+].CC(C)=O.[C:9](Cl)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH3:18][C:19]1[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[C:20]=1[NH2:21]>O>[CH3:18][C:19]1[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[C:20]=1[NH:21][C:2]([NH:3][C:9](=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[S:1]

Participants

6

Reactant 4

HCID 180Acetone2×HCID 68962,6-DimethylanilineHCID 7412Benzoyl chlorideHCID 15666Ammonium thiocyanate

Product 1

HCID 878336n-[(2,6-dimethylphenyl)carbamothioyl]benzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 51.0 g. (0.68 mole) of ammonium thiocyanate in 300 ml. acetone is added 86.8 g. (0.62 mole) of benzoyl chloride. The reaction mixture is refluxed for about 5 min. and then 81 g. (0.62 mole) of 2,6-dimethylaniline in 200 ml. acetone is added at a rate to maintain reflux. The mixture is refluxed for 11/2 hours, cooled, poured into 11/2 liters of ice and water, filtered to obtain 1-(2,6-dimethylphenyl)-3-benzoylthiourea.

Workup

  1. temperatureThe reaction mixture is refluxed for about 5 min.
  2. temperatureto maintain
  3. temperaturereflux
  4. temperatureThe mixture is refluxed for 11/2 hours
  5. temperaturecooled
  6. filtrationfiltered

Sources & evidence

ORD record
ord-340772175c274000b8e209b74054a711
Source dataset
uspto-grants-1977_05
Patent number
US04025652

Reaction notes

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