Benzene, 1-isothiocyanato-4-nitro- → N-Cyano-N'-(4-nitrophenyl)thiourea

HRID 847174

Reaction equation

HRID 847174 reaction equation
[N:1]#[C:2][NH2:3].[Na].[N+:5]([C:8]1[CH:13]=[CH:12][C:11]([N:14]=[C:15]=[S:16])=[CH:10][CH:9]=1)([O-:7])=[O:6]>C(O)C>[C:2]([NH:3][C:15]([NH:14][C:11]1[CH:10]=[CH:9][C:8]([N+:5]([O-:7])=[O:6])=[CH:13][CH:12]=1)=[S:16])#[N:1]

Participants

4

Reactant 2

HCID 75044Benzene, 1-isothiocyanato-4-nitro-HCID 57375518Cyanamidnatrium

Product 1

HCID 14569042N-Cyano-N'-(4-nitrophenyl)thioureaYield 61.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The suspension of monosodium cyanamide (6.4 g, 100 mmol) in absolute ethanol (170 mL) was slowly treated with (4-nitrophenyl)isothiocyanate (12.5 mL, 104.5 mmol). 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. temperatureheated at 75° C. for 4 hours
  2. temperatureThe reaction was cooled to room temperature
  3. filtrationthe colorless solid was filtered
  4. washwashed with ethanol

Sources & evidence

ORD record
ord-dbe4af745a2a47ab910cb1248befce9f
Source dataset
uspto-grants-1992_08
Patent number
US05140031

Linked notes

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