Dimethylformamide → HCID 18174712, compound

HRID 395637Notes

Reaction equation

HRID 395637 reaction equation
Cl[C:2]1[O:3][C:4]([CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[N:6]=1.[CH3:22][C:23]1[NH:24][CH:25]=[CH:26][N:27]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[F:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]2[N:6]=[C:2]([N:24]3[CH:25]=[CH:26][N:27]=[C:23]3[CH3:22])[O:3][C:4]=2[CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 127492-MethylimidazoleHCID 18174687Ethyl 2-chloro-4-(4-fluorophenyl)-5-oxazolebutanoate

Product 1

HCID 18174712HCID 18174712, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 2-chloro-4-(4-fluorophenyl)-5-oxazolebutanoate (3.11 g), 2-methylimidazole (2.46 g), potassium carbonate (4.15 g) and N,N-dimethylformamide (25 ml) was stirred at 120-130° C. for 2 hours. The reaction mixture was poured into water (100 ml) and extracted with ethyl acetate (150 ml×2). The organic layer was dried over anhydrous magnesium sulfate. The organic layer was concentrated, the residue was subjected to silica gel column chromatography, and ethyl 4-(4-fluorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolebutanoate was obtained as an oil (3.47 g, 57%) from an ethyl acetate-hexane (1:1, v/v)-eluted fraction. Conversion to the hydrochloride and the subsequent recrystallization from hexane-ethyl acetate gave pale yellow prisms. Melting point 140-145° C.

Workup

  1. extractionextracted with ethyl acetate (150 ml×2)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-54b184731d3a4ee8a828437f1e9fcff1
Source dataset
uspto-grants-2003_08
Patent number
US06605629B1

Reaction notes

Loading…