Ethyl Acetate → HCID 20154474, compound

HRID 2413913Notes

Reaction equation

HRID 2413913 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[C:14]1([CH3:23])[CH:19]=[CH:18][C:17]([C:20](Cl)=[O:21])=[CH:16][CH:15]=1.[OH-].[Na+].C(OCC)(=O)C>C1C=CC=CC=1.O>[CH3:23][C:14]1[CH:19]=[CH:18][C:17]([C:20]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:7]=2)=[O:21])=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 134054-Methylbenzoyl ChlorideHCID 14798Sodium HydroxideHCID 225219p-Aminophenylacetic acid ethyl ester

Product 1

HCID 20154474HCID 20154474, compoundYield 72.5%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 962WaterSolvent2×

Procedure

10 g of ethyl 4-aminophenylacetate was dissolved in 120 ml of benzene and to this was further added 25 ml of water. To this solution were added dropwise a solution of 8.6 g of p-toluoyl chloride dissolved in 20 ml of benzene and a solution of 2.4 g of 93% NaOH dissolved in 25 ml of water simultaneously under stirring over 15 minutes. After completion of the dropwise addition, the solution was stirred for 3 hours and allowed to stand overnight. After adding 200 ml of ethyl acetate, the oil layer was separated, washed with 1N-HCl solution and with a saturated solution of sodium chloride, and dried over anhydrous sodium sulfate. After distilling off the solvent, the residue was recrystallized from benzene-n-hexane to give 12 g of ethyl 4-(4-methylbenzoylamino)phenylacetate.

Workup

  1. additionAfter completion of the dropwise addition
  2. stirringthe solution was stirred for 3 hours
  3. waitto stand overnight
  4. customthe oil layer was separated
  5. washwashed with 1N-HCl solution and with a saturated solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationAfter distilling off the solvent
  8. customthe residue was recrystallized from benzene-n-hexane

Sources & evidence

ORD record
ord-9ca9d2f6630e4295a16529e2cbb4f54a
Source dataset
uspto-grants-1988_01
Patent number
US04720506

Reaction notes

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