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

HRID 1416044Notes

Reaction equation

HRID 1416044 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][CH:19]=[C:18]([N+:22]([O-])=O)[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:18]1[CH:17]=[C:16]([CH:21]=[CH:20][CH:19]=1)[CH2:15][N:14]1[C:10]([S:9][C:4]2[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=2)=[C:11]([CH:27]([CH3:29])[CH3:28])[N:12]=[C:13]1[CH2:25][OH:26]

Participants

5

Reactant 2

HCID 4740321H-Imidazole-2-methanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-((3-nitrophenyl)methyl)-HCID 178418361HCID 178418361, compound

Product 1

HCID 4740331H-Imidazole-2-methanol, 1-((3-aminophenyl)methyl)-5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

In ethyl acetate was dissolved 64 mg of 5-(3,5-dichlorophenylthio)-2-hydroxymethyl-4-isopropyl-1-(m-nitrobenzyl)-1H-imidazole (103b), and platinum sulfided carbon was added. After replacement with hydrogen atomosphere, the mixture was catalytically hydrogenated under atmospheric pressure at room temperature. After 3 hours, the mixture was filtered through Celite, the filtrate was distilled off under reduced pressure, and diethyl ether was added. Crystals precipitated were filtered, and 25 mg of Compound I-118 was obtained (yield 42%). mp 145-148° C.

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, and diethyl ether
  5. additionwas added
  6. customCrystals precipitated
  7. filtrationwere filtered
  8. customwas obtained (yield 42%)

Sources & evidence

ORD record
ord-9bc3056dc16a46518d2321d0f0867119
Source dataset
uspto-grants-1999_06
Patent number
US05910506

Reaction notes

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