Sodium hydride → HCID 21507487, compound

Participants

Reaction Steps

A 50% oil dispersion of NaH (7.8 g; 0.16 mole) is added to a stirred suspension of 26 g (0.16 mole) of 1H-pyrido[2,3-b][1,4]thiazin-2(3H)-one in 525 ml of toluene and the mixture gradually warmed, effervescence occurs at about 90°. After heating to reflux for 45 minutes, the mixture is cooled to 30°, treated with 120 ml (0.22 mole) of a 1.8 N toluene solution of 3-dimethylaminopropyl chloride and refluxed for 4 hours. After standing overnight, the mixture is worked up as described in Example 1, part A, to give 23 g of crude base. This is combined with 10 g of base from an earlier experiment and distilled; yield, 27.3 g; bp. 166°-169°/0.2 mm.

Provenance & Evidence