1-Amino-2-phenylthio-2-propanol → 5-{4-[2-(3-Phenylthio-2-hydroxypropylamino)propoxy]benzyl}thiazolidine-2,4-dione

HRID 2294287Notes

Reaction equation

HRID 2294287 reaction equation
[C:1]1([S:7][CH2:8][CH:9]([OH:12])[CH2:10][NH2:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=[C:14]([CH3:31])[CH2:15][O:16][C:17]1[CH:30]=[CH:29][C:20]([CH2:21][CH:22]2[S:26][C:25](=[O:27])[NH:24][C:23]2=[O:28])=[CH:19][CH:18]=1.C([BH3-])#N.[Na+]>CO>[C:1]1([S:7][CH2:8][CH:9]([OH:12])[CH2:10][NH:11][CH:14]([CH3:31])[CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]([CH2:21][CH:22]3[S:26][C:25](=[O:27])[NH:24][C:23]3=[O:28])=[CH:29][CH:30]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1137321-Amino-2-phenylthio-2-propanolHCID 5003444Sodium cyanoborohydrideHCID 218321505-[4-(2-Oxopropoxy)benzyl]thiazolidine-2,4-dione

Product 1

HCID 214747875-{4-[2-(3-Phenylthio-2-hydroxypropylamino)propoxy]benzyl}thiazolidine-2,4-dioneYield 36.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A procedure similar to that described in Example 2 was repeated, except that 2.95 g of 3-phenylthio-2-hydroxypropylamine (prepared as described in Preparation 87), 3 g of 5-[4-(2-oxopropoxy)benzyl]thiazolidine-2,4-dione, 1.0 g of sodium cyanoborohydride and 100 ml of anhydrous methanol were used, to give 1.74 g of the title compound, melting at 176° C. to 177° C.

Sources & evidence

ORD record
ord-db70fcc6f90e43629cdc53b8b2f9681c
Source dataset
uspto-grants-1997_11
Patent number
US05688823

Reaction notes

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