Dimethylformamide → HCID 10926471, compound

HRID 2300689Notes

Reaction equation

HRID 2300689 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([N:18]3[CH:22]=[CH:21][N:20]=[C:19]3[CH3:23])[O:11][C:12]=2[CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:31][CH3:32].CN(C)C=O>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([N:18]3[CH:22]=[CH:21][N:20]=[C:19]3[CH3:23])[O:11][C:12]=2[CH2:13][CH2:14][C:15]([O:17][CH2:31][CH3:32])=[O:16])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 11034933HCID 11034933, compound

Product 1

HCID 10926471HCID 10926471, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolepropionic acid(500 mg), potassium carbonate(310 mg), iodoethane(350 mg) and N,N-dimethylformamide(10 ml) was stirred at room temperature for 16 hours. Water was added to the mixture, and the resulting mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water, and dried(MgSO4). The solvent was evaporated and the crystals thus precipitated were collected by filtration. These were recrystallized from acetone-hexane to give colorless of ethyl 4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolepropionate(495 mg, 91%). mp 70-71° C.

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water, and dried(MgSO4)
  3. customThe solvent was evaporated
  4. customthe crystals thus precipitated
  5. filtrationwere collected by filtration
  6. customThese were recrystallized from acetone-hexane

Sources & evidence

ORD record
ord-bd7378bece6549488c7838f135b7e0df
Source dataset
uspto-grants-2002_12
Patent number
US06498179B1

Reaction notes

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