Methanol → HCID 21431239, compound

Participants

Reaction Conditions

Reaction Steps

To 50 ml of methanol in a 125 ml erlenmeyer flask stirred with a magnetic stirrer was slowly added 3.1 grams (0.075 moles) of 57% sodium hydride. The reaction mixture was cooled back to 25° C. and 12.7 grams (0.075 moles) of 2-t-butylazo-2-isocyanatopropane (from Example XIV) was added dropwise over 5 minutes. The reaction mixture was stirred for approximately 1 hour, poured into 200 ml water and the product extracted with pentane. The pentane extract was washed with water, 10% NaHCO3 solution, dried over anhydrous Na2SO4, filtered and the pentane evaporated under reduced pressure to leave 11.8 grams (78% crude yield) of a yellow liquid. The product contained a strong carbonyl band at approximately 1740 cm-1 and a sharp NH band at approximately 3375 cm-1 in its infrared spectrum and there was no isocyanate band at 2225 cm-1.

Provenance & Evidence