Chloride → Sodium methanethiolate

Temperature

-10 °C

Acetaldoxime (30 g., 0.5 mole) was dissolved in 200 g. of a solvent mixture containing 175 g. of water and 25 g. of ethylene glycol, and the solution was cooled to -5° to -10° C. Over a period of 20-30 minutes, 30 g. of chlorine was introduced to to the solution with good agitation. During chlorination, the reaction temperature was maintained at -5° to -10° C. An additional 6 g. 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 acethydroxamoyl chloride solution at -10° C. over a 15-20 minute period. The reaction mixture was stirred for an additional 15 minutes and then neutralized to pH 7.5 with a 50-percent caustic solution. The crystalline methyl hydroxythioacetimidate was recovered at -10° C. by filtration. The methyl hydroxythioacetimidate was reslurred in hexane, filtered and dried to obtain 47 gram of methylhydroxythioacetimidate mp 87°-89° C. This represented a 90% yield.

1. additionof a solvent mixture containing 175 g
2. temperatureDuring chlorination, the reaction temperature was maintained at -5° to -10° C
3. additioncontaining 40 g
4. stirringThe reaction mixture was stirred for an additional 15 minutes
5. filtrationThe crystalline methyl hydroxythioacetimidate was recovered at -10° C. by filtration
6. filtrationfiltered
7. customdried

ORD record

ord-d2e7be0bbfb0429fa0ec9cdb6e4de4e9

Source dataset

uspto-grants-1979_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04144261