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

HRID 1416068
Notes
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Reaction equation

HRID 1416068 reaction equation
[C:1]([O:4][CH2:5][CH2:6][C:7]1[N:8]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([N+:31]([O-])=O)=[CH:27][CH:26]=2)[C:9]([S:15][C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[CH:17]=2)=[C:10]([CH:12]([CH3:14])[CH3:13])[N:11]=1)(=[O:3])[NH2:2].[H][H]>C(OCC)(=O)C.[Pt]>[NH2:31][C:28]1[CH:27]=[CH:26][C:25]([CH2:24][N:8]2[C:9]([S:15][C:16]3[CH:17]=[C:18]([Cl:23])[CH:19]=[C:20]([Cl:22])[CH:21]=3)=[C:10]([CH:12]([CH3:13])[CH3:14])[N:11]=[C:7]2[CH2:6][CH2:5][O:4][C:1](=[O:3])[NH2:2])=[CH:30][CH:29]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 4740691H-Imidazole-2-ethanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-((4-nitrophenyl)methyl)-, carbamate (ester)HCID 178418361HCID 178418361, compound

Product 1

HCID 4740701H-Imidazole-2-ethanol, 1-((4-aminophenyl)methyl)-5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-, carbamate (ester)

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalyst
HCID 8857
Ethyl Acetate
Solvent

Procedure

In 10 ml of ethyl acetate was dissolved 220 mg (0.43 mmol)of 2-(2-carbamoyloxyethyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(p-nitrobenzyl)-1H-imidazole (128a), and 120 mg of platinum sulfided carbon was added at room temperature. Hydrogen gas was introduced for 7 hours under stirring, and the mixture was worked up. The reaction mixture was filtered through Celite under reduced pressure, and the filtrate was distilled off. The residual oil was treated with ether for crystallization to give Compound I-140 (yield 95%).

Workup

  1. additionwas added at room temperature
  2. filtrationThe reaction mixture was filtered through Celite under reduced pressure
  3. distillationthe filtrate was distilled off
  4. additionThe residual oil was treated with ether for crystallization
  5. customto give Compound I-140 (yield 95%)

Sources & evidence

ORD record
ord-1c456e43f8a542b38abf3007eadb2e15
Source dataset
uspto-grants-1999_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05910506

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes