1,4-Dibromobutane → 3-(4-Bromobutyl)-1,3-thiazolidine-2,4-dione
Reaction equation
[Na].[S:2]1[CH2:6][C:5](=[O:7])[NH:4][C:3]1=[O:8].[Br:9][CH2:10][CH2:11][CH2:12][CH2:13]Br>CN(C)C=O>[Br:9][CH2:10][CH2:11][CH2:12][CH2:13][N:4]1[C:5](=[O:7])[CH2:6][S:2][C:3]1=[O:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The 2,4-thiazolidinedione sodium salt (13.91 g., 0.1 mole) is added to a solution of 1,4-dibromobutane (64.77 g., 0.3 mole) in 500 ml. of dry dimethylformamide. After stirring the mixture at room temperature for a 16 hr. period, the resulting clear solution is concentrated in vacuo and residual material dissolved in chloroform, filtered, and concentrated in vacuo to an amber oil. Distillation of the oil affords 20.62 g. (81% yield) of 3-(4-bromobutyl)-2,4-thiazolidinedione, b.p. 105°-115° C. at 0.02 mmHg.
Workup
- concentrationperiod, the resulting clear solution is concentrated in vacuo and residual material
- dissolutiondissolved in chloroform
- filtrationfiltered
- concentrationconcentrated in vacuo to an amber oil
- distillationDistillation of the oil
- customaffords 20.62 g
Sources & evidence
- ORD record
- ord-36630187808c40098768ea1fe11b59f3
- Source dataset
- uspto-grants-1983_01
- Patent number
- US04367335
Reaction notes
Loading…