Nitric Acid → N-(2-nitrooxyethyl)-4-thiazolecarboxamide

Temperature

5 °C

Fuming nitric acid (12.8 ml) was added dropwise to acetic anhydride (27.4 ml) with stirring and ice-sodium chloride cooling at 10° C. for 1 minute, and the mixture was stirred for 10 minutes at the same temperature. Continuously, a solution of N-(2-hydroxyethyl)-4-thiazolecarboxamide (25.0 g) in dry chloroform (35 ml) was added dropwise thereto with stirring and cooling at 5° C. for 10 minutes and the mixture was stirred for hour at the same temperature. The reaction mixture was poured into a mixture of sodium bicarbonate (100 g) and ice-water (1.0 kg) and then extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The solvent was concentrated under reduced pressure and the residual solid was recrystallized from a mixture of diisopropyl ether and methanol (3:2) to give colorless crystals of N-(2-nitrooxyethyl)-4-thiazolecarboxamide (10.17 g).

1. stirringthe mixture was stirred for 10 minutes at the same temperature
2. stirringwith stirring
3. stirringthe mixture was stirred for hour at the same temperature
4. extractionextracted with ethyl acetate
5. washThe extract was washed with a saturated aqueous solution of sodium chloride
6. dry with materialdried over magnesium sulfate
7. concentrationThe solvent was concentrated under reduced pressure
8. customthe residual solid was recrystallized from a mixture of diisopropyl ether and methanol (3:2)

ORD record

ord-b341f5b151eb4e9ab9c0fef59535ca24

Source dataset

uspto-grants-1991_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05010093