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)
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]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
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
- additionwas added at room temperature
- filtrationThe reaction mixture was filtered through Celite under reduced pressure
- distillationthe filtrate was distilled off
- additionThe residual oil was treated with ether for crystallization
- customto give Compound I-140 (yield 95%)
Sources & evidence
- ORD record
- ord-b0f986653a8f4a8b9d48d3789b75bf75
- Source dataset
- uspto-grants-2000_11
- Patent number
- US06147097
Reaction notes
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