4-Nitrobenzyl chloride → Pseudourea, 2-(p-nitrobenzyl)-2-thio-, hydrochloride

HRID 583909Notes

Reaction equation

HRID 583909 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][Cl:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:12][C:13]([NH2:15])=[S:14]>C(O)C>[CH:6]1[C:7]([CH2:8][S:14][C:13]([NH2:15])=[NH:12])=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1.[ClH:9]

Participants

4

Reactant 2

HCID 74824-Nitrobenzyl chlorideHCID 2723790Thiourea

Product 1

HCID 78062Pseudourea, 2-(p-nitrobenzyl)-2-thio-, hydrochlorideYield 90.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-nitrobenzylchloride (Aldrich, 85.8 g, 0.5 mol) and thiourea (Aldrich, 38.1 g, 0.5 mol) in ethanol (250 ml) was heated to reflux, under nitrogen, for 2.5 h. The reaction mixture was allowed to cool to ambient temperature and the precipitate was filtered off. The solid was washed with ethanol and diethylether and then dried in vacuo to give the title compound as a white solid (112.4 g, 90.8%). δH [2H6]—DMSO 4.72 (2H, s); 7.74 (2H, d, 9.4 Hz); 8.25 (2H, d, 9.4 Hz); 9.41 (3H, bds).

Workup

  1. temperaturewas heated
  2. temperatureto reflux, under nitrogen, for 2.5 h
  3. filtrationthe precipitate was filtered off
  4. washThe solid was washed with ethanol and diethylether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-7952c07f2dee4a9e8dc0d66322dae100
Source dataset
uspto-grants-2005_08
Patent number
US06924297B2

Reaction notes

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