4-Chlorophenyl isothiocyanate → HCID 178505525, compound

HRID 2221069Notes

Reaction equation

HRID 2221069 reaction equation
Cl.[NH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)=O.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]=[C:21]=[S:22])=[CH:16][CH:15]=1.C(=O)([O-])O.[Na+]>C(O)C>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[C:4]([C:6]3[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=3)=[CH:3][N:2]=[C:21]2[SH:22])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 164804-Chlorophenyl isothiocyanateHCID 516892Sodium BicarbonateHCID 132906662-Amino-1-(4-fluorophenyl)ethan-1-one hydrochloride

Product 1

HCID 178505525HCID 178505525, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-amino-1-(4-fluoro-phenyl)-ethanone hydrochloride (5.0 g, 26.5 mmol), 4-chlorophenyl isothiocyanate (4.49 g, 26.5 mmol) and sodium hydrogencarbonate (3.3 g, 39.7 mmol) in ethanol (100 mL) was heated at 90° C. for 2 hours. The solvent was removed under reduce pressure. The resulting residue was re-suspended in aqueous 1N sodium hydroxide (50 mL) and heated at 100° C. overnight. The hot mixture was filtered, cooled and carefully acidifed with aqueous 6N HCl. The resulting mixture was filtered to give 1-(4-chloro-phenyl)-5-(4-fluoro-phenyl)-1H-imidazole-2-thiol (8.0 g, 26.3 mmol) as a yellow solid after drying.

Workup

  1. customThe solvent was removed
  2. temperatureheated at 100° C. overnight
  3. filtrationThe hot mixture was filtered
  4. temperaturecooled
  5. filtrationThe resulting mixture was filtered

Sources & evidence

ORD record
ord-5e8dc25979d7432aa6549dd53c53bddd
Source dataset
uspto-grants-2008_05
Patent number
US07368467B2

Reaction notes

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