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 1416042Notes

Reaction equation

HRID 1416042 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 atomosphere, the mixture was catalytically hydrogenated under atmospheric pressure at room temperatures 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. filtrationthe mixture was filtered through Celite
  3. distillationthe filtrate was distilled off under reduced pressure
  4. additionto the residue, diethyl ether was added
  5. filtrationThe precipitated crystals were filtered

Sources & evidence

ORD record
ord-bb3f760ac37a4cd7855b5f725bd2cf2a
Source dataset
uspto-grants-1999_06
Patent number
US05910506

Reaction notes

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