Imidazole → HCID 86760440, compound

HRID 350747Notes

Reaction equation

Cl[C:2]1[O:3][C:4]([CH2:14][CH2:15][C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][P:26]([O:31][CH2:32][CH3:33])([O:28][CH2:29][CH3:30])=[O:27])=[CH:21][CH:20]=2)=[O:17])=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[N:6]=1.[NH:34]1[CH:38]=[CH:37][N:36]=[CH:35]1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]2[N:6]=[C:2]([N:34]3[CH:38]=[CH:37][N:36]=[CH:35]3)[O:3][C:4]=2[CH2:14][CH2:15][C:16]([NH:18][C:19]2[CH:20]=[CH:21][C:22]([CH2:25][P:26]([O:28][CH2:29][CH3:30])([O:31][CH2:32][CH3:33])=[O:27])=[CH:23][CH:24]=2)=[O:17])=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 3-[2-chloro-4-(4-chlorophenyl)-5-oxazolyl]-N-[4-(diethylphosphonomethyl)phenyl]propionamide (0.40 g), imidazole (0.20 g), potassium carbonate (0.41 g) and N,N-dimethylformamide (5 ml) was stirred at 120° C. for 2 hrs. The reaction mixture was poured into water, and the precipitated crystals were collected by filtration through a glass filter. The obtained crystals were washed with water and dried by ventilation. Recrystallization from acetone-isopropyl ether gave 3-[4-(4-chlorophenyl)-2-(1-imidazolyl)-5-oxazolyl]-N-[4-(diethylphosphonomethyl)phenyl]propionamide as pale-yellow prism crystals (0.33 g, 78%). melting point: 196–197° C.

Workup

filtrationthe precipitated crystals were collected by filtration through a glass
filtrationfilter
washThe obtained crystals were washed with water
customdried by ventilation
customRecrystallization from acetone-isopropyl ether

Sources & evidence

ORD record: ord-b168209374c442ea8361707ecdae0fc0
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07183276B2

Reaction notes

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