Dimethylformamide → HCID 10926471, compound

HRID 567179Notes

Reaction equation

HRID 567179 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(500mg), potassium carbonate(310 mg), iodoethane(350mg) 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 15 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(495mg, 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 15 crystals thus precipitated
  5. filtrationwere collected by filtration
  6. customThese were recrystallized from acetone-hexane

Sources & evidence

ORD record
ord-6d239a9a1e5e445489f655c17ae5d371
Source dataset
uspto-grants-2001_01
Patent number
US06177452B1

Reaction notes

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