Dimethylformamide → 3-(4-Bromobutyl)-4-thiazolidinone

A mixture of 4-oxothiazolidine (25 g,) dimethylformamide (500 ml), and KOH (27.16 g) was stirred under N2 at room temperature for 1.5 hours. To the resulting mixture was added 1,4-dibromobutane (101 ml) and stirring was continued at room temperature for 44 hours. The reaction mixture was poured into H2O (1000 ml) and the aqueous mixture was extracted three times with 300 ml portions of ethyl acetate. The combined extracts were washed with H2O (300 ml) and brine (300 ml), dried over Na2SO4, and concentrated in vacuo to an oil. HPLC of a 44.95 g aliquot yielded 7.15 g of an oil which upon distillation yielded a clear liquid, b.p. 134°-137° C/0.12 mmHg.

1. stirringstirring
2. waitwas continued at room temperature for 44 hours
3. extractionthe aqueous mixture was extracted three times with 300 ml portions of ethyl acetate
4. washThe combined extracts were washed with H2O (300 ml) and brine (300 ml)
5. dry with materialdried over Na2SO4
6. concentrationconcentrated in vacuo to an oil
7. distillationHPLC of a 44.95 g aliquot yielded 7.15 g of an oil which upon distillation
8. customyielded a clear liquid, b.p. 134°-137° C/0.12 mmHg

ORD record

ord-f5fbe84acd0d425890172681cdda472c

Source dataset

uspto-grants-1991_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05041445