Beta-Alanine → Methyl 2-carboxyethyldithiocarbamate

β-Alanine (17.8 g., 0.2 mol.) was added to a solution of 22.4 g. (0.4 mol.) of potassium hydroxide in 500 ml. of water at 25°. Carbon disulfide (12.2 ml., 0.2 mol.) was added and the reaction mixture was refluxed for three hours. The mixture was cooled, 28.4 g. (0.2 mol.) of methyl iodide and 500 ml. of ethanol were added and the resulting mixture was stirred for 30 minutes. The precipitate was collected by filtration, the filtrate was concentrated and the aqueous residue was combined with the solid material and brought to pH 8.5-9 by addition of 10% aqueous sodium hydroxide. The resulting suspension was extracted with ethyl acetate. Ethyl acetate was added to the aqueous phase which was then acidified to pH 1.5 with 6N hydrochloric acid. The layers were separated and the aqueous phase was extracted with ethyl acetate. The ethyl acetate extracts were combined, dried (MgSO4) and evaporated to dryness to give methyl 2-carboxyethyldithiocarbamate.

1. customat 25°
2. temperaturethe reaction mixture was refluxed for three hours
3. temperatureThe mixture was cooled
4. filtrationThe precipitate was collected by filtration
5. concentrationthe filtrate was concentrated
6. additionbrought to pH 8.5-9 by addition of 10% aqueous sodium hydroxide
7. extractionThe resulting suspension was extracted with ethyl acetate
8. additionEthyl acetate was added to the aqueous phase which
9. customThe layers were separated
10. extractionthe aqueous phase was extracted with ethyl acetate
11. dry with materialdried (MgSO4)
12. customevaporated to dryness

ORD record

ord-1250061c6bf742d3bb1159de27181034

Source dataset

uspto-grants-1980_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04220644