Hydrochloric Acid → HCID 13280073, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(4-aminobenzenesulphonamido)-N-(3-imidazol-1-ylpropyl)benzamide (11.0 g; hereinbefore prepared in Example 16) in a mixture of concentrated hydrochloric acid (9.5 ml) and water (50 ml) was cooled to between 0° C. and 5° C. whilst a solution of sodium nitrite (2.09 g) in water (15 ml) was added dropwise over 15 minutes. A solution of potassium iodide (4.58 g) in water (10 ml) was then added over 30 minutes, maintaining a temperature between 0° C. and 10° C. The mixture was then heated at 95° C. for 15 minutes. The resultant solution was cooled and adjusted to pH 8 by dropwise addition of 10% w/v aqueous sodium hydroxide solution. The solid precipitate was collected, washed with water and recrystallised from ethyl acetate to give 2-(4-iodobenzenesulphonamido)-N-(3-imidazol-1-ylpropyl)benzamide in the form of a pale-yellow solid, m.p. 162°-166° C. (yield: 3.4 g).

Provenance & Evidence