Dimethylformamide → HCID 18174732, compound

HRID 395666Notes

Reaction equation

HRID 395666 reaction equation
Cl[C:2]1[O:3][C:4]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]([F:25])=[CH:17][CH:16]=2)=[C:5]([CH2:7][CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:6]=1.[CH3:26][C:27]1[NH:28][CH:29]=[CH:30][N:31]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[F:25][C:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:15]([C:4]2[O:3][C:2]([N:28]3[CH:29]=[CH:30][N:31]=[C:27]3[CH3:26])=[N:6][C:5]=2[CH2:7][CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 127492-MethylimidazoleHCID 18174750HCID 18174750, compound

Product 1

HCID 18174732HCID 18174732, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of ethyl 2-chloro-5-(4-fluoro-1-naphthyl)-4-oxazolebutanoate (700 mg), 2-methylimidazole (821 mg), potassium carbonate (1.38 g) and N,N-dimethylformamide (10 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 and concentrated. The residue was subjected to silica gel column chromatography, and ethyl 5-(4-fluoro-1-naphthyl)-2-(2-methyl-1-imidazolyl)-4-oxazolebutanoate was obtained as an oil (675 mg, 77%) from an ethyl acetate-hexane (1:1, v/v)-eluted fraction.

Workup

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

Sources & evidence

ORD record
ord-6f27138880fb448d8ed9ffd2114e1d95
Source dataset
uspto-grants-2003_08
Patent number
US06605629B1

Reaction notes

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