1-[4-(2-Dimethylamino-ethylamino)-3-nitrophenyl]-3-(4-phenoxyphenyl)-1,3-dihydroimidazol-2-one → 1-[3-Amino-4-(2-dimethylaminoethylamino)phenyl]-3-(4-phenoxyphenyl)-1,3-dihydroimidazol-2-one
Reaction equation
[CH3:1][N:2]([CH3:34])[CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH:16]=[CH:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:19][CH:18]=3)[C:13]2=[O:30])=[CH:8][C:7]=1[N+:31]([O-])=O>ClCCl.C(O)(=O)C.[Zn]>[NH2:31][C:7]1[CH:8]=[C:9]([N:12]2[CH:16]=[CH:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)=[CH:19][CH:18]=3)[C:13]2=[O:30])[CH:10]=[CH:11][C:6]=1[NH:5][CH2:4][CH2:3][N:2]([CH3:34])[CH3:1]Participants
5
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Procedure
Zinc dust (250 mg) was added to a solution of 1-[4-(2-dimethylamino-ethylamino)-3-nitrophenyl]-3-(4-phenoxyphenyl)-1,3-dihydroimidazol-2-one (50 mg) in dichloromethane (10 ml) and glacial acetic acid (1 ml). After 10 minutes, solids were removed by filtration and the filtrate was washed with saturated sodium carbonate solution. The organic phase was dried over magnesium sulfate and concentrated. The product with the molecular weight of 429.53 (C25H27N5O2); MS (ESI): 430 ([M+H]+), was obtained in this way.
Workup
- customsolids were removed by filtration
- washthe filtrate was washed with saturated sodium carbonate solution
- dry with materialThe organic phase was dried over magnesium sulfate
- concentrationconcentrated
- customMS (ESI): 430 ([M+H]+), was obtained in this way
Sources & evidence
- ORD record
- ord-adca3358e96b49a3acfa98a756ae33aa
- Source dataset
- uspto-grants-2006_11
- Patent number
- US07141561B2
Reaction notes
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