Propyl mercaptan → HCID 21529711, compound

Participants

Reaction Steps

To 200 ml. of a methanol solution containing 18.2 grams (0.275 moles) of 85% potassium hydroxide pellets in a 11/2 liter jacketed reactor equipped with a mechanical stirrer, thermometer, condenser connected to a bubbler filled with sodium hypochlorite, was added 20.0 grams (0.263 moles) of 1-propanethiol from a pressure equalizing dropping funnel. After the addition of the mercaptan the reaction mixture was stirred for an additional 1/2 hour and then 45.5 grams (0.25 moles) of 88.9% 2-t-butylazo-2-chloropropane was added dropwise over 5 minutes controlling the reaction temperature at 22°C ± 3°C by running cold water through the reactor jacket. The reaction was stirred for an additional 1 hour at 25°C, 5 grams (0.0625 moles) of 50% NaOH added along with 400 mls. of water. The product was extracted with 200 mls. of pentane, the pentane layer separated and washed with 50 ml. of 5% NaOH for 5 minutes, 50 mls. of 10% NaOH for 5 minutes, and then 50 ml. portions of water, 5% HCl, 10% HCl, saturated NaHCO3 solution, dried over anhydrous sodium sulfate, filtered, and the pentane evaporated under reduced pressure to leave 45.9 grams (91.4%) of crude 2-t-butylazo-2-propylthiopropane. Gas chromatographic analysis indicated there was small amounts of 2-t-butylazo-2-methoxypropane and propyl disulfide present in the product.

Provenance & Evidence