2-Mercaptoacetamide → HCID 12620545, compound

Sodium (0.878 g) was dissolved in absolute ethanol (150 ml) under an inert atmosphere. Thioglycolamide (3.47 g) (prepared as described by Sokol and Ritter, J.A.C.S. 70 3517 (1948)) was added and, when practically all the amide had dissolved, bromoacetaldehyde diethyl acetal (11.5 ml) was added. The mixture was heated at 60°-65° C. for 7 hours, cooled and filtered, and the filtrate evaporated under reduced pressure. The residue was dissolved in ethyl acetate (100 ml) and brine (50 ml), the layers separated and the brine extracted with ethyl acetate (50 ml). The combined ethyl acetate extracts were dried over Na2SO4 and evaporated under reduced pressure to yield an oil. Chromatography on silica (50 g), eluting with ethyl acetate/petrol, provided the title compound (6 g) as an oil. νmax (CHCl3) 3500, 3400 and 1690 cm-1 ; δ(CDCl3) 1.20 (6H, t, J 7 Hz, --CH2CH3 ), 2.80 (2H, d, J 5 Hz, >CHCH2S--), 3.25 (2H, s, --SCH2CO--), 3.58 (4H, 2q J 7 Hz, --OCH2CH3), 4.62 (1H, t, J 5 Hz, --CHCH2S--), 7.00 (2H, s, --CONH2); Found 207.0951 (M+) C8H17NO3S requires 207.0929.

1. temperatureThe mixture was heated at 60°-65° C. for 7 hours
2. temperaturecooled
3. filtrationfiltered
4. customthe filtrate evaporated under reduced pressure
5. dissolutionThe residue was dissolved in ethyl acetate (100 ml)
6. custombrine (50 ml), the layers separated
7. extractionthe brine extracted with ethyl acetate (50 ml)
8. dry with materialThe combined ethyl acetate extracts were dried over Na2SO4
9. customevaporated under reduced pressure
10. customto yield an oil
11. washChromatography on silica (50 g), eluting with ethyl acetate/petrol

ORD record

ord-4d0e097fb61c45c3b1a5f802004d5703

Source dataset

uspto-grants-1983_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04372962