Ammonium Hydroxide → 4'-[(6-Hydroxyhexyl)methylamino]-4-methylsulfonylazobenzene

Participants

Reaction Steps

A stirred suspension of 150 g (0.88 mol) of 4-methylsulfonylaniline in 1 liter of 20% hydrochloric acid at 0°-3° C. was treated dropwise with a solution of 66.5 g (0.96 mol) of sodium nitrite in 200 mL of water. N-(6-Hydroxyhexyl)-N-methylaniline (Example 1, 218 g, 1.05 mol) was added slowly, maintaining the temperature below 5° C., and the mixture was stirred for 1 hour. Sodium acetate (119 g, 0.88 mol) was added and stirring was continued for 3 hours. Concentrated ammonium hydroxide (250 mL) was added, and the mixture was stirred for 64 hours. The precipitated product was recrystallized successively from ethanol, from toluene, and then from toluene/isopropanol to produce 160 g (47%) of a red solid, mp 114°-116° C.

Provenance & Evidence