1,4-Dibromobutane → 3-(4-Bromobutyl)-1,3-thiazolidine-2,4-dione

HRID 1164131Notes

Reaction equation

HRID 1164131 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

HCID 80561,4-DibromobutaneHCID 867387272,4-Thiazolidinedione sodium salt

Product 1

HCID 130598253-(4-Bromobutyl)-1,3-thiazolidine-2,4-dioneYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

  1. concentrationperiod, the resulting clear solution is concentrated in vacuo and residual material
  2. dissolutiondissolved in chloroform
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo to an amber oil
  5. distillationDistillation of the oil
  6. customaffords 20.62 g

Sources & evidence

ORD record
ord-36630187808c40098768ea1fe11b59f3
Source dataset
uspto-grants-1983_01
Patent number
US04367335

Reaction notes

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