Water → HCID 53649841, compound

HRID 46771Notes

Reaction equation

HRID 46771 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([S:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:11]([CH2:13][C:14]([OH:16])=[O:15])[N:12]=2)=[CH:4][CH:3]=1.[CH2:24](Br)[CH3:25].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]([S:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[C:11]([CH2:13][C:14]([O:16][CH2:24][CH3:25])=[O:15])[N:12]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6332Ethyl BromideHCID 8471TriethylamineHCID 544691282-p-Chlorophenyl-5-phenylthio-4-oxazoleacetic acid

Product 1

HCID 53649841HCID 53649841, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3.6 g of 2-p-chlorophenyl-5-phenylthio-4-oxazoleacetic acid in 10 ml of dimethylformamide were added 4 ml of ethyl bromide and 4 ml of triethylamine. The mixture was stirred at room temperature for 4 hours. To the reaction mixture were added water and ethyl acetate and the resulting mixture was shaken. The organic layer was successively washed with water, diluted hydrochloric acid and water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Recrystallization of the residue from ethanol gave 3.2 g of the title compound, melting at 109°-110° C.

Workup

  1. stirringthe resulting mixture was shaken
  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. customRecrystallization of the residue from ethanol

Sources & evidence

ORD record
ord-fb41941b04b545ddba1cba47715ecde5
Source dataset
uspto-grants-1979_11
Patent number
US04175130

Reaction notes

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