4-Chlorophenyl isothiocyanate → N-(4-Chlorophenyl)-N'-cyanothiourea

HRID 976236Notes

Reaction equation

HRID 976236 reaction equation
[N:1]#[C:2][NH2:3].[Na].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]=[C:13]=[S:14])=[CH:8][CH:7]=1>C(O)C>[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([NH:3][C:2]#[N:1])=[S:14])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 164804-Chlorophenyl isothiocyanateHCID 57375518Cyanamidnatrium

Product 1

HCID 11805994N-(4-Chlorophenyl)-N'-cyanothioureaYield 86.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The suspension of monosodium cyanamide (1.9 g, 29.4 mmol) in absolute ethanol (5 mL) was slowly treated with 4-chlorophenylisothiocyanate (5.0 g, 29.4 mmol). The reaction was allowed to stir at room temperature for one hour and then heated at 75° C. for four hours. The reaction was cooled to room temperature and the colorless solid was filtered and washed with ethanol to give the title compound (5.4 g), mp>250° C.

Workup

  1. temperatureheated at 75° C. for four hours
  2. temperatureThe reaction was cooled to room temperature
  3. filtrationthe colorless solid was filtered
  4. washwashed with ethanol

Sources & evidence

ORD record
ord-ec5b337ad6ff45189ab98bde3205f48e
Source dataset
uspto-grants-1997_03
Patent number
US05612323

Reaction notes

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