Water → N-(((2,6-Dichlorophenyl)amino)thioxomethyl)benzamide

HRID 1283748Notes

Reaction equation

HRID 1283748 reaction equation
[S-:1][C:2]#[N:3].[NH4+].[C:5](Cl)(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Cl:14][C:15]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:16]=1[NH2:17].O>CC(C)=O>[Cl:14][C:15]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:16]=1[NH:17][C:2]([NH:3][C:5](=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[S:1]

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 118462,6-DichloroanilineHCID 15666Ammonium thiocyanate

Product 1

HCID 702451N-(((2,6-Dichlorophenyl)amino)thioxomethyl)benzamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To 51.8 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 minutes and then 100 g (0.62 mole) of 2,6-dichloro aniline in 200 ml acetone is added at a rate to maintain reflux. The mixture is refluxed for 1 1/2 hours, cooled, poured into 1 1/2 liter of ice and water, filtered to obtain 1-(2,6-dichlorophenyl)-3-benzoylthiourea.

Workup

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

Sources & evidence

ORD record
ord-105d99103f7e472d9414d3a83716595e
Source dataset
uspto-grants-1976_08
Patent number
US03976643

Reaction notes

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