4-Chlorophenyl isothiocyanate → HCID 178505525, compound

HRID 1985861Notes

Reaction equation

HRID 1985861 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, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-amino-1-(4-fluoro-phenyl)-ethanone hydrochloride (1 eq), 4-chlorophenyl isothiocyanate (1 eq) and sodium hydrogencarbonate (1.5 eq) in ethanol is heated at 90° C. for 2 hours. The solvent is removed under reduce pressure. The resulting residue is re-suspended in aqueous 1N sodium hydroxide and heated at 100° C. overnight. The hot mixture is filtered, cooled and carefully acidified with aqueous 6N HCl. The resulting mixture is filtered to give 1-(4-chloro-phenyl)-5-(4-fluoro-phenyl)-1H-imidazole-2-thiol.

Workup

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

Sources & evidence

ORD record
ord-d0a65ade30a143b4a8e2137276bcd0d7
Source dataset
uspto-grants-2009_06
Patent number
US07547717B2

Reaction notes

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