反应详情

Solid 4-(2-acetoxy-ethyl)-8-nitro-naphthalene-1-sulfonyl chloride (39.64 g, 111 mmol) was added to an ice-cold, 6.8 M solution of ammonia in methanol (408 mL, 277 mmol). The cooling bath was removed, the reaction flask was stoppered, and the reaction was stirred at room temperature. After 4 days, the dark amber solution was concentrated under vacuum to a dark gum. The residue was triturated vigorously shaken with water (300 mL) to give a solid which was washed with water (150 mL) then ether (150 mL) and dried under vacuum. The resulting brown solid was recrystallized from isopropanol (300 mL) to afford 4-(2-hydroxy-ethyl)-8-nitro-naphthalene-1-sulfonamide (27.79 g) as tan flakes.

1. customThe cooling bath was removed
2. concentrationthe dark amber solution was concentrated under vacuum to a dark gum
3. customThe residue was triturated vigorously
4. stirringshaken with water (300 mL)
5. customto give a solid which
6. washwas washed with water (150 mL)
7. dry with materialether (150 mL) and dried under vacuum
8. customThe resulting brown solid was recrystallized from isopropanol (300 mL)