Ethylene Oxide → HCID 21823167, compound

Participants

Reaction Steps

8 Grams of ethylene oxide was dissolved at room temperature in 80 ml. of methanol. To this solution, 8 mg. of 1,2,4,5-tetrahydro-3,2-benzoxazepine were added. After standing overnight, the reaction mixture was refluxed for one hour and then evaporated in vacuo. The residue was distilled at 120° C./0.1 mm Hg. giving 9.3 g. of 2-(2-hydroxyethyl)-1,2,4,5-tetrahydro-3,2-benzoxazepine. To 2.9 g. of the latter compound in 160 ml. of chloroform, 2.47 g. of sodium cyanate was added, then hydrogen chloride was bubbled therethrough for about 30 minutes under stirring. The reaction mixture was then transferred to a separatory funnel and treated with 90 ml. aqueous of 5 percent sodium hydroxide. The organic layer was separated, washed with a saturated solution of sodium chloride and dried over sodium sulfate. After evaporation of the chloroform solution, the residue was crystallized from diisopropyl ether giving 1.82 g. of 2-(2-carbamyloxyethyl)-1,2,4,5-tetrahydro-3,2-benzoxazepine, m.p. 110°-111° C.

Provenance & Evidence