2-Bromo-4'-nitroacetophenone → 3-[2-(4-Nitrophenyl)-2-oxoethyl]-1,3-thiazolidine-2,4-dione

HRID 56613

Reaction equation

HRID 56613 reaction equation
[K].[S:2]1[CH2:6][C:5](=[O:7])[NH:4][C:3]1=[O:8].Br[CH2:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)=[O:12]>CC(C)=O>[N+:19]([C:16]1[CH:15]=[CH:14][C:13]([C:11](=[O:12])[CH2:10][N:4]2[C:5](=[O:7])[CH2:6][S:2][C:3]2=[O:8])=[CH:18][CH:17]=1)([O-:21])=[O:20]

Participants

4

Reactant 2

HCID 668402-Bromo-4'-nitroacetophenoneHCID 878923181,3-Thiazolidine-2,4-dione potassium salt

Product 1

HCID 115508943-[2-(4-Nitrophenyl)-2-oxoethyl]-1,3-thiazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

A little at a time, 1.3 g (8.4 mmol) of 1,3-thiazolidine-2,4-dione potassium salt were added to a solution of 2.0 g (8.2 mmol) of 2-bromo-1-(4-nitrophenyl)ethanone in 80 ml of acetone, and the mixture was stirred at 60° C. for 1 h. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in water/dichloromethane. After phase separation, the organic phase was dried (sodium sulphate), filtered, concentrated under reduced pressure and dried. Yield: 2.3 g (98% of theory)

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in water/dichloromethane
  3. customAfter phase separation
  4. dry with materialthe organic phase was dried (sodium sulphate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customdried

Sources & evidence

ORD record
ord-d1249409e06848c98d2c30682af412d3
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Linked notes

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