Water → HCID 13713893, compound

HRID 4386

Reaction equation

HRID 4386 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][CH:7]2[S:11][C:10](=[O:12])[NH:9][C:8]2=[O:13])=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:19][C:20]1[N:21]=[C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[O:23][CH:24]=1.O>CN(C)C=O>[C:25]1([C:22]2[O:23][CH:24]=[C:20]([CH2:19][O:1][C:2]3[CH:15]=[CH:14][C:5]([CH2:6][CH:7]4[S:11][C:10](=[O:12])[NH:9][C:8]4=[O:13])=[CH:4][CH:3]=3)[N:21]=2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 35511964-(Chloromethyl)-2-phenyl-1,3-oxazoleHCID 101983975-(4-Hydroxybenzyl)thiazolidine-2,4-dione

Product 1

HCID 13713893HCID 13713893, compoundYield 56.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 5-(4-hydroxybenzyl)-2,4-thiazolidinedione (9.4 g) in N,N-dimethylformamide (80 ml) was added 60% sodium hydride in oil (3.4 g), and the mixture was stirred for 30 minutes. Then, a solution of 4-chloromethyl-2-phenyloxazole (9.6 g) in N,N-dimethylformamide (20 ml) was added dropwise thereto at room temperature. After being stirred at 70° C. for 1 hour, the reaction solution was poured into water, and the aqueous mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concentrated to give 5-[4-(2-phenyl-4-oxazolylmethoxy)benzyl]-2,4-thiazolidinedione (9.1 g, 47.4%). Recrystallization from ethanol yielded colorless needles. m.p. 188°-189° C. Elemental analysis for C20H16N2O4S; Calcd.: C, 63.15; H, 4.24; N, 7.36. Found: C, 63.19; H, 4.16; N, 7.23.

Workup

  1. customat room temperature
  2. stirringAfter being stirred at 70° C. for 1 hour
  3. extractionthe aqueous mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-35e63bd3939a469295f57ada34255d08
Source dataset
uspto-grants-1988_02
Patent number
US04725610

Linked notes

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