Potassium Carbonate → Methyl 4-(3,4-dichlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolepropionate

HRID 563097Notes

Reaction equation

Cl[C:2]1[O:3][C:4]([CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([Cl:14])[CH:8]=2)[N:6]=1.[CH3:21][C:22]1[NH:23][CH:24]=[CH:25][N:26]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:14][C:9]1[CH:8]=[C:7]([C:5]2[N:6]=[C:2]([N:23]3[CH:24]=[CH:25][N:26]=[C:22]3[CH3:21])[O:3][C:4]=2[CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:12]=[CH:11][C:10]=1[Cl:13]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of methyl 2-chloro-4-(3,4-dichlorophenyl)-5-oxazolepropionate (1.00 g), 2-methylimidazole (0.82 g), potassium carbonate (0.69 g), and N,N-dimethylformamide (20 ml) was stirred at 120° C. for 1 hour. The reaction mixture was poured into ice water (100 ml). The precipitated crystals were filtered, washed in sequence with water and isopropyl ether, and air-dried to give crystals of methyl 4-(3,4-dichlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolepropionate. Recrystallization from ethyl acetate-isopropyl ether gave pale yellow prisms (0.82 g, 72%). Melting point 116-117° C.

Workup

filtrationThe precipitated crystals were filtered
washwashed in sequence with water and isopropyl ether
customair-dried

Sources & evidence

ORD record: ord-80da2585a0b74c808e81f1a19e01c2ea
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067453B2

Reaction notes

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