Dimethylformamide → 1H-Imidazole-4-carboxaldehyde, 5-chloro-2-propyl-

HRID 1756818Notes

Reaction equation

CN(C)[CH:3]=[O:4].[CH2:6]([C:9]1[NH:13][C:12](=O)[CH2:11][N:10]=1)[CH2:7][CH3:8].O=P(Cl)(Cl)[Cl:17].[OH-].[Na+]>ClC1C=CC=CC=1>[CH2:6]([C:9]1[NH:13][C:12]([Cl:17])=[C:11]([CH:3]=[O:4])[N:10]=1)[CH2:7][CH3:8]

Participants

Conditions

Temperature: 100 °C

Procedure

N,N-dimethylformamide (7.04 g, 96.3 mmol) was added to a mixture of 2-n-propyl-3,5-dihydroimidazol-4-one (4.49 g, 35.6 mmol) and POCl3 (14.76 g, 96.3 mmol) in chlorobenzene (40 ml) at 100° C. The mixture was heated for 2 hours at 100° C., cooled and poured on 40 g of ice. The mixture was adjusted to pH 1 by the addition of 30 percent sodium hydroxide solution (22.5 ml) and the phases were separated. The aqueous phase was extracted twice with 40 ml of ethyl acetate each and the combined organic phases were washed with water (20 ml) and filtered on silica gel. After removal of the solvent from the filtrate, 2.79 g of a light brown solid was obtained. Recrystallization from ethyl acetate/petroleum ether yielded the title compound (2.04 g, 33 percent). The product had a melting point of 133.3° to 137.5° C. Other data concerning the product was:

Workup

temperaturecooled
customthe phases were separated
extractionThe aqueous phase was extracted twice with 40 ml of ethyl acetate each and the combined organic phases
washwere washed with water (20 ml)
filtrationfiltered on silica gel
customAfter removal of the solvent from the filtrate

Sources & evidence

ORD record: ord-66012a0783994fe4995cf5617782da19
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05442075

Reaction notes

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