Benzenemethanol, 4-amino-alpha-(aminomethyl)-3,5-dichloro- → 5-[4-[2-[(4-Amino-3,5-dichloro-beta-hydroxyphenethyl)amino]propyl]benzyl]thiazolidine-2,4-dione
Reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([CH:9]([OH:12])[CH2:10][NH2:11])=[CH:4][C:3]=1[Cl:13].[CH2:14]([C:18]1[CH:31]=[CH:30][C:21]([CH2:22][CH:23]2[S:27][C:26](=[O:28])[NH:25][C:24]2=[O:29])=[CH:20][CH:19]=1)[C:15]([CH3:17])=O>>[NH2:1][C:2]1[C:3]([Cl:13])=[CH:4][C:5]([CH:9]([OH:12])[CH2:10][NH:11][CH:15]([CH3:17])[CH2:14][C:18]2[CH:19]=[CH:20][C:21]([CH2:22][CH:23]3[S:27][C:26](=[O:28])[NH:25][C:24]3=[O:29])=[CH:30][CH:31]=2)=[CH:6][C:7]=1[Cl:8]Participants
3
Procedure
5-[4-[2-[(4-Amino-3,5-dichloro-β-hydroxyphenethyl)amino]propyl]benzyl]thiazolidine-2,4-dione was prepared as a 46:54 mixture of diastereoisomers, mp. 195°-201° C., from 2-(4-amino-3,5-dichlorophenyl)-2-hydroxy ethylamine and 5-(4-acetonylbenzyl)thiazolidine-2,4-dione in an analogous manner to that described in Example 5
Sources & evidence
- ORD record
- ord-df3c57176d444f62a4e310d2b390b2f4
- Source dataset
- uspto-grants-1992_10
- Patent number
- US05153210
Reaction notes
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