Hydrochloric Acid → (Z)-4-amino-N-hydroxy-1,2,5-oxadiazole-3-carbonimidoyl chloride

Participants

Reaction Conditions

Reaction Steps

A solution of 3 M of hydrogen chloride in water (190 mL) was treated with 4-amino-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide [J. Heterocycl. Chem. (1965), 2, 253] (7.3 g, 0.051 mol) at 0° C. The reaction mixture was treated with enough 12 M hydrogen chloride (˜19 mL) to dissolve the solid and then treated with a solution of sodium nitrite (4.4 g, 0.063 mol) in water (24 mL) dropwise while maintaining an internal temperature at 0-5° C. with an ice/brine bath. The reaction mixture was stirred at 0° C. for 1.5 h and filtered to yield a beige solid. Purification of the crude mixture by preparative HPLC gave the desired product (1.7 g, 21%) as an off-white solid.

Provenance & Evidence