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

HRID 47939Notes

Reaction equation

HRID 47939 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>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

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 127492-MethylimidazoleHCID 23431803Methyl 2-chloro-4-(3,4-dichlorophenyl)-5-oxazolepropionate

Product 1

HCID 23431809Methyl 4-(3,4-dichlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolepropionate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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 h. The reaction mixture was poured into iced water (100 mL) and the precipitated crystals were collected by filtration, washed with water and then with isopropyl ether and air-dried to give the title compound as crystals. Recrystallization from ethyl acetate-isopropyl ether gave pale-yellow prism crystals (0.82 g, 72%). melting point: 116-117° C.

Workup

  1. filtrationthe precipitated crystals were collected by filtration
  2. washwashed with water
  3. dry with materialwith isopropyl ether and air-dried

Sources & evidence

ORD record
ord-9b18b199b9ae4723b48770f2d52c3b1f
Source dataset
uspto-grants-2004_03
Patent number
US06699995B1

Reaction notes

Loading…