HCID 19846612, compound → HCID 178507978, compound

HRID 2413752Notes

Reaction equation

HRID 2413752 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([NH:9][C:10]([NH:12][CH2:13][CH:14](OC)OC)=[S:11])=[CH:4][C:3]=1[F:19]>S(=O)(=O)(O)O.O>[NH2:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([N:9]2[CH:14]=[CH:13][N:12]=[C:10]2[SH:11])=[CH:4][C:3]=1[F:19]

Participants

4

Reactant 1

HCID 19846612HCID 19846612, compound

Product 1

HCID 178507978HCID 178507978, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

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. temperaturewas refluxed for three hours
  2. temperatureThe mixture then is cooled
  3. filtrationthe solid that forms is filtered
  4. washwashed with water
  5. customdried
  6. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-e0971c79718a43da8e107f4887c8f962
Source dataset
uspto-grants-1988_01
Patent number
US04719223

Reaction notes

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