Water → Ethyl 2-p-chlorophenyl-5-(2,5-dimethylphenoxy)-4-oxazoleacetate

HRID 46769Notes

Reaction equation

HRID 46769 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([O:17][C:18]3[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][C:19]=3[CH3:25])=[C:11]([CH2:13][C:14]([OH:16])=[O:15])[N:12]=2)=[CH:4][CH:3]=1.[CH2:26](N(CC)CC)[CH3:27].C(Br)C.O>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([O:17][C:18]3[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][C:19]=3[CH3:25])=[C:11]([CH2:13][C:14]([O:16][CH2:26][CH3:27])=[O:15])[N:12]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6332Ethyl BromideHCID 8471TriethylamineHCID 203856742-p-Chlorophenyl-5-(2,5-dimethylphenoxy)-4-oxazoleacetic acid

Product 1

HCID 20385693Ethyl 2-p-chlorophenyl-5-(2,5-dimethylphenoxy)-4-oxazoleacetate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.80 g of 2-p-chlorophenyl-5-(2,5-dimethylphenoxy)-4-oxazoleacetic acid in 8 ml of dimethylformamide were added 1 ml of triethylamine and 1.5 ml of ethyl bromide. The mixture was stirred at 35°-40° C. for 90 minutes. The reaction mixture was poured into water and ethyl acetate and shaken with a separate funnel. The organic layer was successively washed with water, diluted hydrochloric acid and water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The white crystalline residue was recrystallized from n-hexane to give 0.68 g of the title compound as white fine needles, melting at 122°-123.5° C.

Workup

  1. stirringshaken with a separate funnel
  2. washThe organic layer was successively washed with water, diluted hydrochloric acid and water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe white crystalline residue was recrystallized from n-hexane

Sources & evidence

ORD record
ord-78d5fb0f79924ff3ba2378b92fb05498
Source dataset
uspto-grants-1979_11
Patent number
US04175130

Reaction notes

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