1H-Imidazole-2-ethanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-((4-nitrophenyl)methyl)- → 1H-Imidazole-2-ethanol, 1-((4-aminophenyl)methyl)-5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-
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][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=3)[C:13]([CH2:25][CH2:26][OH:27])=[N:12][C:11]=2[CH:28]([CH3:30])[CH3:29])[CH:5]=[C:6]([Cl:8])[CH:7]=1>C(OCC)(=O)C.[Pt]>[NH2:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][N:14]2[C:10]([S:9][C:4]3[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=3)=[C:11]([CH:28]([CH3:30])[CH3:29])[N:12]=[C:13]2[CH2:25][CH2:26][OH:27])=[CH:17][CH:18]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
In 10 ml of ethyl acetate was dissolved 124 mg (0.26 mmol)of the nitrobenzyl compound (126a), and 120 mg of platinum sulfided carbon was added at room temperature. H2 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 residue was purified by silica gel column chromatography (ethyl acetate), the resulting oil was treated with ether for crystallization to give Compound I-139 (yield 33%), mp 142-145° C.
Workup
- additionwas added at room temperature
- additionH2 gas was introduced for 7 hours
- filtrationThe reaction mixture was filtered through Celite under reduced pressure
- distillationthe filtrate was distilled off
- customThe residue was purified by silica gel column chromatography (ethyl acetate)
- additionthe resulting oil was treated with ether for crystallization
- customto give Compound I-139 (yield 33%), mp 142-145° C.
Sources & evidence
- ORD record
- ord-c58fe8107c4b458c8c55d01d273fb4da
- Source dataset
- uspto-grants-1999_06
- Patent number
- US05910506
Reaction notes
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