Dimethylformamide → 1-(4-phenylbutyl)-1H-imidazole-2-carboxamide

Temperature

-78 °C

Reaction under N2 atmosphere. A mixture of DIPA (0.455 mol) in THF (500 ml) was stirred at −78° C. Butyllithium, 2.5M/hexane (0.390 mol) was added dropwise at −40° C. The mixture was stirred for 15 min, then re-cooled to −78° C. A solution of 1-(4-phenylbutyl)-1H-imidazole, prepared according to the procedure described in J. Chem. Soc., Perkin Trans., 1 (1975), 17, 1670–1671, (0.325 mol) in THF (350 ml) was added dropwise at −60° C. The mixture was stirred for one hour, then re-cooled to −78° C. This mixture was added dropwise to a mixture of N,N-dimethylformamide (0.390 mol, dry, p.a.) in THF (500 ml), stirred at −78° C. The reaction mixture was stirred for one hour at −78° C., then allowed to warm to room temperature while stirring overnight. A saturated aqueous NH4Cl solution (400 ml) was added and this mixture was extracted with THF. The separated organic layer was dried, filtered and the solvent evaporated, yielding 74.2 g of 1-(4-phenylbutyl)-1H-imidazole-2-carboxamide (interm. 18).

1. customReaction under N2 atmosphere
2. stirringThe mixture was stirred for 15 min
3. temperaturere-cooled to −78° C
4. stirringThe mixture was stirred for one hour
5. temperaturere-cooled to −78° C
6. stirringstirred at −78° C
7. stirringThe reaction mixture was stirred for one hour at −78° C.
8. temperatureto warm to room temperature
9. stirringwhile stirring overnight
10. extractionthis mixture was extracted with THF
11. customThe separated organic layer was dried
12. filtrationfiltered
13. customthe solvent evaporated

ORD record

ord-696b82fd9a0a4806818870df0e9948e3

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07087595B2