Hydrochloric Acid → 5-(4-Hydroxybenzyl)-3-triphenylmethylthiazolidine-2,4-dione

HRID 1742505Notes

Reaction equation

HRID 1742505 reaction equation
C([O:4][C:5]1[CH:37]=[CH:36][C:8]([CH2:9][CH:10]2[S:14][C:13](=[O:15])[N:12]([C:16]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:11]2=[O:35])=[CH:7][CH:6]=1)(=O)C.Cl>CO.C1(C)C=CC=CC=1>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:9][CH:10]2[S:14][C:13](=[O:15])[N:12]([C:16]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:11]2=[O:35])=[CH:36][CH:37]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 11027585HCID 11027585, compound

Product 1

HCID 28181265-(4-Hydroxybenzyl)-3-triphenylmethylthiazolidine-2,4-dioneYield 83.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

A solution of 2.99 g of a 28% w/v methanolic solution of sodiumamethoxide in 10 ml of methanol was added dropwise, whilst ice-cooling, to a solution of 7.86 g of 5-(4-acetoxybenzyl)-3-triphenylmethyl-thiazolidine-2,4-dione [prepared as described in step (c) above] in 70 ml of toluene, and the resulting mixture was stirred at room temperature for 1 hour, after which it was allowed to stand overnight at the same temperature. The pH of the reaction mixture was then adjusted to a value of 4 by the addition of 1N aqueous hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure, and the crystals which appeared in the residue were collected, washed with hexane and dried, to give 6.0 g of the title compound.

Workup

  1. waitto stand overnight at the same temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was then removed by distillation under reduced pressure
  6. customwere collected
  7. washwashed with hexane
  8. customdried

Sources & evidence

ORD record
ord-ebfbb6c80cd447a28787da56f35b864a
Source dataset
uspto-grants-1994_08
Patent number
US05338855

Reaction notes

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