Thiazolidinedione → HCID 16392506, compound
Reaction equation
[H-].[Na+].[S:3]1[CH2:7][C:6](=[O:8])[NH:5][C:4]1=[O:9].[Br:10][CH:11](Br)[CH3:12]>CN(C=O)C>[Br:10][CH2:11][CH2:12][N:5]1[C:6](=[O:8])[CH2:7][S:3][C:4]1=[O:9]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a 50 ml 3-neck flask, NaH (60% in mineral oil) (0.614 g, 25.6 mmole) was taken in DMF (20 mL) under N2 atmosphere and cooled to 0° C. To this, thiazolidine-2,4-dione (2.0 g, 1.707 mmole) followed by dibromoethane (1.61 mL, 18.78 mmole) were added at 0° C. and the reaction mixture was stirred at room temperature for 2 hrs. After completion of the reaction, ice was added to the reaction mixture and product was extracted with EtOAc. The combined organic layer was washed with water, dried over Na2SO4 and evaporated to get the crude product which was subjected for the column purification. The crude compound was purified using column purification using 60-120 mesh size neutral silica by eluting the compound with 20-25% EtOAc in hexanes to yield 1.5 g of 3-(2-bromoethyl)thiazolidine-2,4-dione.
Workup
- additionwere added at 0° C.
- customAfter completion of the reaction, ice
- additionwas added to the reaction mixture and product
- extractionwas extracted with EtOAc
- washThe combined organic layer was washed with water
- dry with materialdried over Na2SO4
- customevaporated
- customto get the crude product which
- customwas subjected for the column purification
- customThe crude compound was purified
- customcolumn purification
- washby eluting the compound with 20-25% EtOAc in hexanes
Sources & evidence
- ORD record
- ord-40b339d017614025a5f4b12dfddc0f90
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09187487B2
Reaction notes
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