1H-Imidazole-2-methanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-((4-nitrophenyl)methyl)- → 1H-Imidazole-2-methanol, 1-((4-aminophenyl)methyl)-5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-

HRID 1857739Notes

Reaction equation

HRID 1857739 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=3)[C:13]([CH2:25][OH:26])=[N:12][C:11]=2[CH:27]([CH3:29])[CH3:28])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[H][H]>C(OCC)(=O)C.[Pt]>[NH2:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][N:14]2[C:10]([S:9][C:4]3[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=3)=[C:11]([CH:27]([CH3:29])[CH3:28])[N:12]=[C:13]2[CH2:25][OH:26])=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 4740291H-Imidazole-2-methanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-((4-nitrophenyl)methyl)-HCID 178418361HCID 178418361, compound

Product 1

HCID 4740301H-Imidazole-2-methanol, 1-((4-aminophenyl)methyl)-5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-Yield 78%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

In ethyl acetate was dissolved 800 mg of 5-(3,5-dichlorophenylthio)-2-hydroxymethyl-4-isopropyl-1-(p-nitrobenzyl)-1H-imidazole (103a), and platinum sulfided carbon was added. After replacement with hydrogen atmosphere, the mixture was catalytically hydrogenated under atmospheric pressure at room temperature. After 1 hour, the mixture was filtered through Celite, the filtrate was distilled off under reduced pressure, and to the residue, diethyl ether was added. The precipitated crystals were filtered, and 579 mg of 1-(p-aminobenzyl)-5-(3,5-dichlorophenylthio)-2-hydroxymethyl-4-isopropyl-1H-imidazole (104a) was obtained (yield 78%). mp 130° C. (decomp.).

Workup

  1. additionwas added
  2. customwas catalytically hydrogenated under atmospheric pressure at room temperature
  3. filtrationthe mixture was filtered through Celite
  4. distillationthe filtrate was distilled off under reduced pressure
  5. additionto the residue, diethyl ether was added
  6. filtrationThe precipitated crystals were filtered

Sources & evidence

ORD record
ord-b3499f3df3a34a6aa4aeb8c0079ddb45
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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