Aminoacetaldehyde dimethyl acetal → HCID 19846612, compound

HRID 2413751Notes

Reaction equation

HRID 2413751 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([N:9]=[C:10]=[S:11])=[CH:4][C:3]=1[F:12].[CH3:13][O:14][CH:15]([O:18][CH3:19])[CH2:16][NH2:17]>ClC(Cl)Cl>[NH2:1][C:2]1[C:3]([F:12])=[CH:4][C:5]([NH:9][C:10]([NH:17][CH2:16][CH:15]([O:18][CH3:19])[O:14][CH3:13])=[S:11])=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 19846610HCID 19846610, compound

Product 1

HCID 19846612HCID 19846612, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 4-amino-3,5-difluorophenyl isothiocyanate in trichloromethane is treated with an equimolar amount of aminoacetaldehyde dimethyl acetal. The solvent is evaporated, and the residue is recrystallized from ethanol to yield N-(4-amino-3,5-difluorophenyl)-N'-(β,β-dimethoxyethyl)thiourea. A suspension of this thiourea in concentrated sulfuric acid and water (1:4) was refluxed for three hours. The mixture then is cooled and the solid that forms is filtered, washed with water, and dried. Recrystallization from ethanol yields 1-(4'-amino-3',5'-difluorophenyl)imidazole-2-thiol.

Workup

  1. customThe solvent is evaporated
  2. customthe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-0637b1780d784fceab5ed4e34569b015
Source dataset
uspto-grants-1988_01
Patent number
US04719223

Reaction notes

Loading…