4-Nitrobenzyl chloride → HCID 178526643, compound

HRID 1387144Notes

Reaction equation

HRID 1387144 reaction equation
Cl.Cl[CH2:3][C:4]1[N:5]=[CH:6][NH:7][CH:8]=1.NC(N)=[S:11].[N+:13]([C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Cl)=[CH:18][CH:17]=1)([O-:15])=[O:14].[OH-].[Na+]>C(O)C.O>[N+:13]([C:16]1[CH:23]=[CH:22][C:19]([CH2:20][S:11][CH2:3][C:4]2[N:5]=[CH:6][NH:7][CH:8]=2)=[CH:18][CH:17]=1)([O-:15])=[O:14]

Participants

7

Reactant 4

HCID 74824-Nitrobenzyl chlorideHCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 178478565HCID 178478565, compound

Product 1

HCID 178526643HCID 178526643, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×

Procedure

A mixture of 1.53 g (10 mmol) of 4-chloromethylimidazole hydrochloride and 0.76 g (10 mmol) of thiourea is brought to reflux in 10 ml of ethanol for 15 min. 5 ml of ethanol, 20 ml of water and 200 mg (1.16 mmol) of 4-nitrobenzyl chloride are added and the mixture is cooled to 0°-10° C. 1.44 g (36 mmol) of a solution of sodium hydroxide in 14 ml of water are added dropwise under nitrogen at 0°-10° C., and the mixture is then stirred for 1 hour at the same temperature and for a further 3 hours at room temperature. The abovementioned is collected and washed with water to provide the title compound, M.p.: 88° C.

Workup

  1. temperaturethe mixture is cooled to 0°-10° C
  2. customThe abovementioned is collected
  3. washwashed with water

Sources & evidence

ORD record
ord-486b420ce189453dbaea86608d6bf3e3
Source dataset
uspto-grants-2001_07
Patent number
USRE037303E1

Reaction notes

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