Methyl Isobutyl Ketone → 3-(2-Nitrophenylmethyl)-2-thiazolidinone

HRID 2108008Notes

Reaction equation

HRID 2108008 reaction equation
[S:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6].C(=O)([O-])[O-].[K+].[K+].[C:13](=O)([O-])O.[K+].[N+:18](C(Br)C1C=CC=CC=1)([O-:20])=[O:19].[CH2:29]([C:33]([CH3:35])=O)[CH:30]([CH3:32])[CH3:31]>O>[N+:18]([C:29]1[CH:33]=[CH:35][CH:13]=[CH:31][C:30]=1[CH2:32][N:3]1[CH2:4][CH2:5][S:1][C:2]1=[O:6])([O-:20])=[O:19]

Participants

7

Reactant 5

HCID 7909Methyl Isobutyl KetoneHCID 11430Potassium CarbonateHCID 974312-ThiazolidinoneHCID 516893Potassium BicarbonateHCID 11356361Nitrobenzylbromide

Product 1

HCID 1319643-(2-Nitrophenylmethyl)-2-thiazolidinoneYield 37%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

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 6.5 g (0.03 mol) of nitrobenzyl bromide is refluxed for 6 hours, then cooled down and thoroughly mixed with 50 ml of water. The mixture is filtered and the clear filtrate is separated. The organic phase is washed with 10 ml of water, dried and evaporated. The oily residue is recrystallized from ethanol to give 2.65 g (37.0%) of the title compound, m.p.: 92°-93° C.

Workup

  1. temperatureis refluxed for 6 hours
  2. temperaturecooled down
  3. filtrationThe mixture is filtered
  4. customthe clear filtrate is separated
  5. washThe organic phase is washed with 10 ml of water
  6. customdried
  7. customevaporated
  8. customThe oily residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-8e5cfbeb71f34778bf07aa59cb31cada
Source dataset
uspto-grants-1990_06
Patent number
US04937252

Reaction notes

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