Water → 4-Oxazoleacetic acid, 5-(4-chlorophenoxy)-2-(4-chlorophenyl)-, ethyl ester

HRID 46766Notes

Reaction equation

HRID 46766 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]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)=[C:11]([CH2:13][C:14]([OH:16])=[O:15])[N:12]=2)=[CH:4][CH:3]=1.[CH2:25](Br)[CH3:26].C(N(CC)CC)C.O>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]([O:17][C:18]3[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=3)=[C:11]([CH2:13][C:14]([O:16][CH2:25][CH3:26])=[O:15])[N:12]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6332Ethyl BromideHCID 8471TriethylamineHCID 203856682-p-Chlorophenyl-5-p-chlorophenoxy-4-oxazoleacetic acid

Product 1

HCID 30520914-Oxazoleacetic acid, 5-(4-chlorophenoxy)-2-(4-chlorophenyl)-, ethyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 33.3 g of 2-p-chlorophenyl-5-p-chlorophenoxy-4-oxazoleacetic acid in 100 ml of dimethylformamide were added 40 ml of ethyl bromide and 40 ml of triethylamine. The mixture was stirred at room temperature for 40 minutes and then allowed to stand overnight. To the resulting mixture were added water and ethyl acetate and then the mixture was shaken. The organic layer was washed successively with water, diluted hydrochloric acid and water, then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was recrystallized from a mixture of n-hexane and ethyl acetate to give 34.3 g of the title compound as white crystals, melting at 70°-72° C.

Workup

  1. waitto stand overnight
  2. stirringthe mixture was shaken
  3. washThe organic layer was washed successively with water, diluted hydrochloric acid and water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from a mixture of n-hexane and ethyl acetate

Sources & evidence

ORD record
ord-eb150dbd2f04454f86efbdf08f079977
Source dataset
uspto-grants-1979_11
Patent number
US04175130

Reaction notes

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