HCID 14839440, compound → 2-(2-Methylaminobenzylthio)imidazole

HRID 1090825Notes

Reaction equation

HRID 1090825 reaction equation
[SH:1][C:2]1[NH:3][CH:4]=[CH:5][N:6]=1.Cl.[CH3:8][NH:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[CH2:12]Cl>C(O)C>[CH3:8][NH:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[CH2:12][S:1][C:2]1[NH:3][CH:4]=[CH:5][N:6]=1

Participants

4

Reactant 2

HCID 14839440HCID 14839440, compoundHCID 178527877HCID 178527877, compound

Product 1

HCID 150274142-(2-Methylaminobenzylthio)imidazoleYield 65.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 693 mg (6.9 mmol) of 2-mercaptoimidazole in 26 ml of ethanol was added 1.33 g (6.9 mmol) of 2-methylaminobenzyl chloride hydrochloride, and the mixture was stirred for 15 min. at room temperature. Ethanol was distilled off under reduced pressure. The residue was made alkaline by addition of saturated aqueous sodium hydrogencarbonate and then to the alkaline solution was added 20 ml of water to precipitate a crystalline product. The product was collected by filtration and washed successively with two portions of water and each one portion of chilled ethanol and ether to give 990 mg of the desired compound as a white crystalline powder, yield 05.5 %.

Workup

  1. distillationEthanol was distilled off under reduced pressure
  2. additionby addition of saturated aqueous sodium hydrogencarbonate
  3. additionto the alkaline solution was added 20 ml of water
  4. customto precipitate a crystalline product
  5. filtrationThe product was collected by filtration
  6. washwashed successively with two portions of water

Sources & evidence

ORD record
ord-a39894b7872642418c9885ea3f09e30f
Source dataset
uspto-grants-1992_01
Patent number
US05082943

Reaction notes

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