Acetyl chloride → 1-(Azidomethyl)-3,5,7-trinitro-1,3,5,7-tetrazocane

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Reaction Conditions

Reaction Steps

A solution of sodium azide (345 g, 5.45 mole) in water (1200 mL) was cooled to 5° C. and with good stirring a solution of acetyl chloride (286 g, 3.64 mol) in methylene chloride (640 mL) was added in 2.5 h, maintaining the temperature at 5° C. with external cooling. The upper aqueous layer was siphoned off and Compound 4 (101 g, 0.294 mol) was added. The mixture was stirred for 3 h at 10°-15° C. and filtered. The white solid was washed with methylene chloride (2×200 mL), water (200 mL), and ether (2×200 mL), and dried in a vacuum oven overnight at 40° C. The yield of Compound 5 was 71 g (79%), m.p. 130°-131° C. IR (KBr) 2080 cm-1 (N3), 1540 cm-1 (N--NO2). HPLC analysis showed a single peak. Analysis calculated for C5H10N10O6 : C,19.61: H,3.27; N,45.75. Found: C,19.99: H,3.28; N,44.99.

Provenance & Evidence