Acetic Acid → 5-{4-[2-(2,5-Dimethyl-4-oxazolyl)-2-hydroxyethoxy]benzyl}-2,4-thiazolidinedione

HRID 4395Notes

Reaction equation

HRID 4395 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1[O:5][C:6]([CH3:27])=[C:7]([C:9](=[O:26])[CH2:10][O:11][C:12]2[CH:25]=[CH:24][C:15]([CH:16]=[C:17]3[S:21][C:20](=[O:22])[NH:19][C:18]3=[O:23])=[CH:14][CH:13]=2)[N:8]=1.C(O)(=O)C>CO.CN(C)C=O>[CH3:3][C:4]1[O:5][C:6]([CH3:27])=[C:7]([CH:9]([OH:26])[CH2:10][O:11][C:12]2[CH:13]=[CH:14][C:15]([CH2:16][CH:17]3[S:21][C:20](=[O:22])[NH:19][C:18]3=[O:23])=[CH:24][CH:25]=2)[N:8]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 539407785-{4-[2-(2,5-Dimethyl-oxazolyl)-2-oxoethoxy]benzylidene}-2,4-thiazolidinedione

Product 1

HCID 137139175-{4-[2-(2,5-Dimethyl-4-oxazolyl)-2-hydroxyethoxy]benzyl}-2,4-thiazolidinedioneYield 97.5%

Reagents, catalysts & solvents 1

HCID 21901440N,N-dimethylformamide methanolSolvent

Procedure

Sodium borohydride (0.16 g) was added to a suspension of 5-{4-[2-(2,5-dimethyl-oxazolyl)-2-oxoethoxy]benzylidene}-2,4-thiazolidinedione (1.5 g) in methanol-N,N-dimethylformamide (1:1, V.V, 40 ml) under ice-cooling. After stirring under ice-cooling for 20 minutes, the reaction solution was poured into ice-water, and the aqueous mixture was made acid with acetic acid, and the crystals which separated out were collected by filtration to give 5-{4-[2-(2,5-dimethyl-4-oxazolyl)-2-hydroxyethoxy]benzyl}-2,4-thiazolidinedione (1.47 g, 97.5%). Recrystallization from chloroform-ethanol afforded colorless prisms, m.p. 223°-224° C. Elemental analysis for C17H16N2O5S, Calcd.: C, 56.66; H, 4.47; N, 7.77. Found: C, 56.36; H, 4.55; N, 7.56.

Workup

  1. temperaturecooling
  2. temperaturecooling for 20 minutes
  3. customthe crystals which separated out
  4. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-7c9f173d9c7d4c9db041ee6af88f9112
Source dataset
uspto-grants-1988_02
Patent number
US04725610

Reaction notes

Loading…