Ammonia → HCID 22457552, compound

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)

ORD record

ord-b4ed599a70f349f79f8cd3374997e2d4

Source dataset

uspto-grants-2002_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06399597B1