Diphenyl carbonate → 3-(4-Methoxybenzyl)thiazolidin-2-one

HRID 2108005Notes

Reaction equation

HRID 2108005 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH:10][CH2:11][CH2:12][SH:13])=[CH:5][CH:4]=1.[C:14](=O)(OC1C=CC=CC=1)[O:15]C1C=CC=CC=1>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][N:10]2[CH2:11][CH2:12][S:13][C:14]2=[O:15])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 7597Diphenyl carbonateHCID 14306201N-(4-methoxybenzyl)-cysteamine

Product 1

HCID 230450983-(4-Methoxybenzyl)thiazolidin-2-oneYield 32.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution containing 4.53 g (0.025 mol) of N-(4-methoxyphenylmethyl)-cysteamine and 5.35 g (0.025 mol) of diphenyl carbonate in 25 ml of ethanol is refluxed under nitrogen for 24 hours, then evaporated. The residue is taken up in ethyl acetate, washed with 2N sodium hydroxide solution until it becomes free from phenol, then washed with water, dried and evaporated. The residue becomes solid under ether. Thus, 1.82 g (32.6%) of the title compound are obtained, m.p.: 84°-86° C.

Workup

  1. temperatureis refluxed under nitrogen for 24 hours
  2. customevaporated
  3. washwashed with 2N sodium hydroxide solution until it
  4. washwashed with water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-9ef934f1ce8042f59c3b127ca83ef784
Source dataset
uspto-grants-1990_06
Patent number
US04937252

Reaction notes

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