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

HRID 1857743Notes

Reaction equation

HRID 1857743 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]=[CH:18][C:17]=3[N+:22]([O-])=O)[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:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[CH2:15][N:14]1[C:10]([S:9][C:4]2[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=2)=[C:11]([CH:27]([CH3:29])[CH3:28])[N:12]=[C:13]1[CH2:25][OH:26]

Participants

5

Reactant 2

HCID 4740341H-Imidazole-2-methanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-((2-nitrophenyl)methyl)-HCID 178418361HCID 178418361, compound

Product 1

HCID 4740351H-Imidazole-2-methanol, 1-((2-aminophenyl)methyl)-5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

In ethyl acetate was dissolved 170 mg of 5-(3,5-dichlorophenylthio)-2-hydroxymethyl-4-isopropyl-1-(o-nitrobenzyl)-1H-imidazole (103c), platinum sulfided carbon was added. After replacement with hydrogen atomosphere, catalytic hydrogenation was performed at atmospheric pressure at room temperature. After 1 hour, the mixture was filtered through Celite, and the Filtrate was distilled off under reduced pressure. To the residue, diethyl ether was added, the precipitated crystals were collected by filteration, and 77 mg of Compound I-119 was obtained (yield 49%).

Workup

  1. additionwas added
  2. customwas performed at 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. customthe precipitated crystals were collected by filteration, and 77 mg of Compound
  7. customwas obtained (yield 49%)

Sources & evidence

ORD record
ord-d2c2e24612f348228029135bcf2328a3
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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