Benzyl Bromide → 3-Phenylmethyl-2-thiazolidinone

HRID 2108004Notes

Reaction equation

HRID 2108004 reaction equation
[S:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6].C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(C(C)=O)C(C)C.O>[C:19]1([CH2:18][N:3]2[CH2:4][CH2:5][S:1][C:2]2=[O:6])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 974312-ThiazolidinoneHCID 516893Potassium Bicarbonate

Product 1

HCID 109213893-Phenylmethyl-2-thiazolidinoneYield 55.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture containing 3.09 g (0.03 mol) of 2-thiazolidinone, 11.2 g of potassium carbonate, 1.8 g of potassium hydrogen carbonate, 0.5 ml of water, 30 ml of methyl isobutyl ketone and 3.0 ml (0.033 mol) of benzyl bromide is refluxed for 7 hours. After cooling down, the reaction mixture is washed twice with 30 ml of water each, the organic phase is dried and evaporated. The yellow oily product (which solidifies on standing) may be purified by column chromatography (by using Kieselgel 60 of 230-400 mesh as sorbent and chloroform as eluent) to give 3.2 g (55.2%) of the title compound, m.p.: 50°-51° C.

Workup

  1. temperatureis refluxed for 7 hours
  2. temperatureAfter cooling down
  3. washthe reaction mixture is washed twice with 30 ml of water each, the organic phase
  4. customis dried
  5. customevaporated
  6. customThe yellow oily product (which solidifies on standing) may be purified by column chromatography (by using Kieselgel 60 of 230-400 mesh as sorbent and chloroform as eluent)

Sources & evidence

ORD record
ord-09dffb13fd044b10b5db815b05a02ee1
Source dataset
uspto-grants-1990_06
Patent number
US04937252

Reaction notes

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