Methanethiol → HCID 20496527, compound

Temperature

-10 °C

Acetaldoxime (30 g., 0.5 mole) was dissolved in 200 g. of water and the solution cooled to -5 to -10° C. Over a period of 20 to 30 minutes, 30 g. of chlorine was introduced into the solution with agitation. During the chlorine addition, the reaction temperature was maintained at -5° to -10° C. An additional 6 grams of chlorine was added in 10 minutes. The mixture was stirred for 10-15 minutes at -10° C. A sodium methyl mercaptide solution was prepared by dissolving methyl mercaptan (25 g, 0.52 mole) in a caustic solution containing 40 g. of sodium hydroxide in 100 g. of water. The mercaptide solution was fed directly into the reaction mixture over a 15 to 20 minute time period while maintaining the temperature at -10° C. The reaction mixture was stirred for an additional 15 minutes and then neutralized to a pH 7.5 by addition of 50% sodium hydroxide solution. Crystaline methyl hydroxythioacetimidate was recovered at -10° C. by filtration. The product was re-slurried in hexane, filtered and dried to obtain 43 grams (83% yield) of methyl hydroxythioacetimidate, mp 87°-88° C.

1. temperaturethe reaction temperature was maintained at -5° to -10° C
2. additioncontaining 40 g
3. temperaturetime period while maintaining the temperature at -10° C
4. stirringThe reaction mixture was stirred for an additional 15 minutes
5. filtrationCrystaline methyl hydroxythioacetimidate was recovered at -10° C. by filtration
6. filtrationfiltered
7. customdried

ORD record

ord-2496ae181155436d8207100ba7132bd4

Source dataset

uspto-grants-1979_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04144261