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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 1857741
Notes
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Reaction equation

HRID 1857741 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 23939PlatinumCatalyst
HCID 8857
Ethyl Acetate
Solvent

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 atmosphere, 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-0a71c98eb99b4dcd80dd32ed84792212
Source dataset
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06147097

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes