Hydrochloric Acid → HCID 20300397, compound

Participants

Reaction Steps

To a stirred solution of the 4-amino-1-cyclohexylbenzotriazole (11.4 g, 0.054 mol) in 75 ml of concentrated hydrochloric acid and 75 ml of water at 5°, was slowly added 4.1 g of sodium nitrite (0.059 mol) in 15 ml of water. On completion of the addition, the reaction mixture was allowed to stir an additional 1/2 hour at 0°-5°. Next the solution was added slowly to an excess of freshly prepared cuprous chloride in 120 ml of concentrated hydrochloric acid also at 0°-5°. On completion of the addition, the reaction came to room temperature over a 21/2 hour period. Then one liter of water was added to the reaction mixture and the crude product which precipitated was collected by filtration, washed with water and air-dried. This material was purified by column chromatography to yield 6.2 g of product, m.p. 141°-144°.

Provenance & Evidence