Diphenyl carbonate → 3-Phenylmethyl-2-thiazolidinone

HRID 2108002Notes

Reaction equation

HRID 2108002 reaction equation
[C:1]1([CH2:7][NH:8][CH2:9][CH2:10][SH:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:12](=O)(OC1C=CC=CC=1)[O:13]C1C=CC=CC=1>C(O)C>[C:1]1([CH2:7][N:8]2[CH2:9][CH2:10][S:11][C:12]2=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 7597Diphenyl carbonateHCID 136802Ethanethiol, 2-benzylamino-

Product 1

HCID 109213893-Phenylmethyl-2-thiazolidinoneYield 56.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution containing 33.6 g (0.2 mol) of N-phenylmethylcysteamine and 42.8 g (0.2 mol) of diphenyl carbonate in 200 ml of ethanol is refluxed under nitrogen for 24 hours, then ethanol is evaporated under reduced pressure. The residue is taken up in ethyl acetate, washed with 2N sodium hydroxide solution until it becomes free of phenol, then washed with water, dried and evaporated. The residue is distilled under reduced pressure to give 21.8 g (56.4%) of the title compound, b.p.: 140° C./1.5 Hgmm, which solidifies under petroleum ether, m.p.: 50°-51° C.

Workup

  1. temperatureis refluxed under nitrogen for 24 hours
  2. customethanol is evaporated under reduced pressure
  3. washwashed with 2N sodium hydroxide solution until it
  4. washwashed with water
  5. customdried
  6. customevaporated
  7. distillationThe residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-69b6cf32a3fe49ae9f07bfa6b5d05cf8
Source dataset
uspto-grants-1990_06
Patent number
US04937252

Reaction notes

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