Acetic Acid → 2-Thenylamine, N,N-bis(2-chloroethyl)-, hydrochloride

One millimole of DCTA-bromide was added to 5 ml of 50% DMF containing 0.2 ml of 1,2-dithioethylene and 0.5 ml of triethylamine. The mixture was incubated under argon for 2 hours at 60°-70° C. After reaction the mixture was diluted with oxygen-free H2O to 50 ml, the pH was adjusted to 4.0-4.5 with glacial acetic acid and the excess HS--CH2 --CH2 --SH was extracted three times with 15 ml benzene by stirring (not shaking). The water phase was then loaded onto a Dowex AG-1 column, 9 ml bed volume. The column was washed with 50 ml of 0.1M acetic acid solution until the flowthrough was thiol free. The DCTA-SH was then eluted with 0.25M HCl. The thiol containing fractions were combined, evaporated to dryness under reduced pressure at 40° C. and the free acid (300 mg) was stored at -20° C. under argon.

1. customAfter reaction the mixture
2. extractionthe excess HS--CH2 --CH2 --SH was extracted three times with 15 ml benzene
3. stirringshaking)
4. washThe column was washed with 50 ml of 0.1M acetic acid solution until the flowthrough
5. washThe DCTA-SH was then eluted with 0.25M HCl
6. customevaporated to dryness under reduced pressure at 40° C.
7. customwas stored at -20° C. under argon

ORD record

ord-add5ed0b1cf749ee9b639277d4a369af

Source dataset

uspto-grants-1990_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04952685