Phenyl Isothiocyanate → N-cyano-N'-phenylthiourea

HRID 1197812Notes

Reaction equation

HRID 1197812 reaction equation
[N:1]#[C:2][NH2:3].[Na].[C:5]1([N:11]=[C:12]=[S:13])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(O)C>[C:2]([NH:3][C:12]([NH:11][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[S:13])#[N:1]

Participants

4

Reactant 2

HCID 7673Phenyl IsothiocyanateHCID 57375518Cyanamidnatrium

Product 1

HCID 4711553N-cyano-N'-phenylthioureaYield 76.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of monosodium cyanamide (6.4 g, 100 mmol) in absolute ethanol (170 mL), phenylisothiocyanate (12.5 mL, 104.5 mmol) was added slowly with stirring at room temperature. The reaction was allowed to stir at room temperature for 1 hour and then heated at 75° C. for 4 hours. The reaction was cooled to room temperature and the colorless solid was filtered and washed with ethanol to give the title A compound (13.6 g), m.p. >250° C.

Workup

  1. additionwas added slowly
  2. stirringto stir at room temperature for 1 hour
  3. temperatureheated at 75° C. for 4 hours
  4. temperatureThe reaction was cooled to room temperature
  5. filtrationthe colorless solid was filtered
  6. washwashed with ethanol

Sources & evidence

ORD record
ord-5b50b4d0b2c94b0cb112d7309d5ce0d4
Source dataset
uspto-grants-1994_01
Patent number
US05278169

Reaction notes

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