Sulfuric Acid → HCID 178434099, compound

A solution of aminotetrazole (0.1 g, 1.1 mmol) in 4 M sulfuric acid (3.0 mL, 12.0 mmol) was cooled to −5° C. To this mixture was then added a cooled solution of sodium nitrite (0.08 g, 1.1 mmol) in 0.5 mL of water. The solution was then added to a solution of 3-amino-5-methylpyrazole (0.2 g, 2.1 mmol) and NaOAc trihydrate (1.5 g, 11 mmol) dissolved in a mixture of water (1 mL) and HOAc (3 mL). After stirring for 2 hours, water (50 mL) was added and the crude material was extracted from the aqueous layer three times with ethyl acetate (150 mL). The combined ethyl acetate solutions were washed with brine, dried over anhydrous MgSO4, filtered and evaporated. The crude material was purified by column chromatography (CHCl3:MeOH:NH4OH=3:1:0.005). The isolated material was then further purified by preparative TLC (CHCl3:MeOH:NH4OH=3:1:0.005) to yield 7 mg (3%) of the title compound as a red solid.

1. extractionthe crude material was extracted from the aqueous layer three times with ethyl acetate (150 mL)
2. washThe combined ethyl acetate solutions were washed with brine
3. dry with materialdried over anhydrous MgSO4
4. filtrationfiltered
5. customevaporated
6. customThe crude material was purified by column chromatography (CHCl3:MeOH:NH4OH=3:1:0.005)
7. customThe isolated material was then further purified by preparative TLC (CHCl3:MeOH:NH4OH=3:1:0.005)

ORD record

ord-de59850e820c4f78ab825c1d2d77b915

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08445694B2