4-Nitroaniline → N-(4-Nitrophenyl)octadecanamide

Participants

Reaction Steps

In a three necked flask equipped with a dropping funnel, a thermometer and a reflux condenser, p-nitroaniline (138 g) was dissolved in a mixed solution of tetrahydrofuran (200 ml) and pyridine (140 ml) in a nitrogen atmosphere. Then, octadecanoyl chloride (333 g) was added dropwise into the three necked flask through the dropping funnel, over a time span of 20 minutes while stirring the reaction mixture. After the completion of the dropping, the reaction mixture was stirred for 2 hours. Then, a solid product was produced. The solid product was filtered and the filtrate was concentrated under a reduced pressure to provide crystals. The crystals were collected and recrystallized from ethanol. 4'-nitro-n-octadecaneanilide (364 g) was obtained. The yield thereof was 90%.

Provenance & Evidence