Cesium carbonate → HCID 21474776, compound

HRID 1901739Notes

Reaction equation

HRID 1901739 reaction equation
Br[CH2:2][C:3](=[O:6])[CH2:4][CH3:5].[OH:7][C:8]1[CH:40]=[CH:39][C:11]([CH2:12][CH:13]2[S:17][C:16](=[O:18])[N:15]([C:19]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:14]2=[O:38])=[CH:10][CH:9]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[O:6]=[C:3]([CH2:4][CH3:5])[CH2:2][O:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:12][CH:13]2[S:17][C:16](=[O:18])[N:15]([C:19]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:14]2=[O:38])=[CH:39][CH:40]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 131561-Bromo-2-butanoneHCID 28181265-(4-Hydroxybenzyl)-3-triphenylmethylthiazolidine-2,4-dione

Product 1

HCID 21474776HCID 21474776, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 7.37 ml of 1-bromo-2-butanone, 20.0 g of 5-(4-hydroxybenzyl)-3-triphenylmethylthiazolidine-2,4-dione, 21.18 g of cesium carbonate and 200 ml of anhydrous acetone was stirred at room temperature for 3 hours. At the end of this time, the acetone was removed by evaporation under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. The ethyl acetate was removed by evaporation under reduced pressure, and the residue was recrystallized from a mixture of ethyl acetate, diethyl ether and diisopropyl ether, to give 19.36 g of the title compound, melting at 155.2° to 156.4° C.

Workup

  1. customAt the end of this time, the acetone was removed by evaporation under reduced pressure, water
  2. additionwas added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with an aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe ethyl acetate was removed by evaporation under reduced pressure
  7. customthe residue was recrystallized from a mixture of ethyl acetate, diethyl ether and diisopropyl ether

Sources & evidence

ORD record
ord-04a07b54085a425aba14097396e722bd
Source dataset
uspto-grants-1996_11
Patent number
US05578620

Reaction notes

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