Difluoroacetic acid → HCID 14551036, compound

Difluoracetic acid was added to a mixture of carbonyl diimidazole (8.4 g, 0.052 mol) and methylene chloride (100 ml) under a nitrogen atmosphere. Gas was evolved and a new solid formed in the reaction. After stirring at room temperature for 30 minutes, 5-amino-2-methoxypyridine (5.7 ml, 0.052 mol) was added over a two-minute period. The reacion was slightly exothermic and was stirred further for another 30 minutes when it was washed with water (100 ml), 5% aqueous acetic acid (2×50 ml), 5% sodium bicarbonate (25 ml); dried over anhydrous magnesium sulfate; filtered; and evaporated in vacuo to give an oil. The oil was extracted with ether and the ether extract on dilution with pentane gave 3.7 g of crude product. This was extracted with ether and diluted with pentane to give 2.0 g of the title compound, m.p. 75°-78° C. The title product was identified by IR, NMR and MS analysis.

1. customa new solid formed in the reaction
2. stirringwas stirred further for another 30 minutes when it
3. washwas washed with water (100 ml), 5% aqueous acetic acid (2×50 ml), 5% sodium bicarbonate (25 ml)
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationfiltered
6. customand evaporated in vacuo
7. customto give an oil
8. extractionThe oil was extracted with ether
9. extractionthe ether extract on dilution with pentane
10. customgave 3.7 g of crude product
11. extractionThis was extracted with ether
12. additiondiluted with pentane

ORD record

ord-9a802cd900e9482bbad0559856ba90ee

Source dataset

uspto-grants-1989_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04845107