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

HRID 27197

Reaction equation

HRID 27197 reaction equation
[S-:1][C:2]#[N:3].[NH4+].[CH2:5](Cl)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Cl:13][C:14]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:15]=1[NH2:16].[OH2:22]>CC(C)=O>[Cl:13][C:14]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:15]=1[NH:16][C:2]([NH:3][C:5](=[O:22])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[S:1]

Participants

6

Reactant 4

HCID 962WaterHCID 7503Benzyl 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 benzyl chloride. The reaction mixture is refluxed for about 5 min. and then 100 g (0.62 mole) of 2,6-dichloroaniline 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-dichlorophenyl)-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-ee423d099bfc46fcb321850ee7ca0ec7
Source dataset
uspto-grants-1980_09
Patent number
US04220658

Linked notes

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