1,1'-Carbonyldiimidazole → 5-(3,5-Dimethyl-3H-imidazol-4-yl)-3-methyl-[1,2,4]oxadiazole

Temperature

80 °C

A solution of 3,5-dimethyl-3H-imidazole-4-carboxylic acid (1.0 g, 7.14 mmol) and 1,1′-carbonyldiimidazole (1.74 g, 10.7 mmol) in DMF (35 ml) was stirred at RT for 3 h. N-hydroxy-acetamidine (0.68 g, 9.18 mmol) was added, the reaction mixture was stirred at 16 h at 80° C., evaporated and dissolved in acetic acid (30 ml). The solution was stirred at 100° C. for 2 h, evaporated, poured into sat. NaHCO3 solution (50 ml) and extracted with dichloromethane (7×30 ml). The combined organic layers were washed with brine (70 ml), dried (MgSO4) and evaporated to give the title compound (0.78 g, 61%) as a white solid, m.p. 95° C. and MS: m/e=178.2 (M+).

1. customevaporated
2. dissolutiondissolved in acetic acid (30 ml)
3. stirringThe solution was stirred at 100° C. for 2 h
4. customevaporated
5. additionpoured into sat. NaHCO3 solution (50 ml)
6. extractionextracted with dichloromethane (7×30 ml)
7. washThe combined organic layers were washed with brine (70 ml)
8. dry with materialdried (MgSO4)
9. customevaporated

ORD record

ord-ea65c1773556478688c304026aa4b719

Source dataset

uspto-grants-2004_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06706707B2