Methyl 2-chloromethylbenzoate → S-(2-Methoxycarbonylbenzyl)isothiourea.hydrochloride

HRID 330450Notes

Reaction equation

HRID 330450 reaction equation
[Cl:1][CH2:2][C:3]1[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].[NH2:13][C:14]([NH2:16])=[S:15]>C(O)C>[CH3:8][O:7][C:5]([C:4]1[CH:9]=[CH:10][CH:11]=[CH:12][C:3]=1[CH2:2][S:15][C:14](=[NH:13])[NH2:16])=[O:6].[ClH:1]

Participants

4

Reactant 2

HCID 118590Methyl 2-chloromethylbenzoateHCID 2723790Thiourea

Product 1

HCID 14275685S-(2-Methoxycarbonylbenzyl)isothiourea.hydrochlorideYield 40.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 196 g of methyl 2-chloromethylbenzoate and 83.7 g of thiourea in 500 ml of ethanol is refluxed for 4 hours. The reaction solution is concentrated under reduced pressure and to the resulting residue is added 300 ml of isopropylalcohol. The precipitated crystals are collected by filtration and dried to give 112.8 g of the title compound.

Workup

  1. concentrationThe reaction solution is concentrated under reduced pressure and to the resulting residue
  2. additionis added 300 ml of isopropylalcohol
  3. filtrationThe precipitated crystals are collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-292e1c87e4da4ab985e86ae03a32c2ab
Source dataset
uspto-grants-1990_01
Patent number
US04897105

Reaction notes

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