Acetyl chloride → HCID 20270846, compound

Participants

Reaction Steps

Dunning and Dunning (J.Chem.Soc., 2925(1950)) have reported that treatment of 1-methoxymethyl-3,5-dinitro-1,3,5-triazacyclohexane with acetyl chloride and acetyl bromide gave 1-chloromethyl-3,5-dinitro-1,3,5-triazacyclohexane and 1-bromomethyl-3,5-dinitro-1,3,5-triazacyclohexane, respectively. This chemistry was applied to the current work on the eight-membered ring derivatives. Treatment of (Compound 3) with acetyl bromide gave a quatitative yield of 1-bromomethyl-3,5,7-trinitro-1,3,5,7-tetrazacyclooctane (Compound 4). Attempts to convert Compound 4 to Compound 5 with sodium azide were unsuccessful. Thus, a novel method Eq. 2 was needed and invented for the conversion of Compound 4 to Compound 5. ##STR2##

Provenance & Evidence