Sodium Hydroxide → HCID 13267761, compound

HRID 2413912Notes

Reaction equation

HRID 2413912 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](Cl)(=[O:18])[CH:15]([CH3:17])[CH3:16].[OH-].[Na+]>C1C=CC=CC=1.O>[C:14]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:7]=1)(=[O:18])[CH:15]([CH3:17])[CH3:16]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 62325Isobutyryl chlorideHCID 225219p-Aminophenylacetic acid ethyl ester

Product 1

HCID 13267761HCID 13267761, compoundYield 88.4%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 962WaterSolvent2×

Procedure

10 g of ethyl 4-aminophenylacetate was dissolved in 100 ml of benzene and to this was added 25 ml of water. To the solution were added dropwise a solution of 6 g of isobutyryl chloride in 20 ml of benzene and a solution of 2.4 g of 93% NaOH in 25 ml of water simultaneously under stirring over 15 minutes. After completion of the dropwise addition, the reaction mixture was stirred for 3 hours and allowed to stand at room temperature overnight. After separating the benzene layer, washing it with 1N-HCl solution and further washing with a saturated solution of sodium chloride, the benzene layer was dried over anhydrous sodium sulfate. After separating sodium sulfate by filteration, the solvent was distilled off under reduced pressure and the residue was dissolved in 30 ml of benzene and crystallized from 90 ml of n-hexane. The formed crystals were separated by filteration and were dried at a temperature below 60° C. under reduced pressure to give 12.3 g of ethyl 4-(isobutyrylamino)phenylacetate (Yield: 88.3%). M.P. 92.5°-93.5° C.

Workup

  1. additionAfter completion of the dropwise addition
  2. waitto stand at room temperature overnight
  3. customAfter separating the benzene layer
  4. washwashing it with 1N-HCl solution
  5. washfurther washing with a saturated solution of sodium chloride
  6. dry with materialthe benzene layer was dried over anhydrous sodium sulfate
  7. customAfter separating sodium sulfate by filteration
  8. distillationthe solvent was distilled off under reduced pressure
  9. dissolutionthe residue was dissolved in 30 ml of benzene
  10. customcrystallized from 90 ml of n-hexane
  11. customThe formed crystals were separated by filteration
  12. customwere dried at a temperature below 60° C. under reduced pressure

Sources & evidence

ORD record
ord-9e6c1ebd33f74c40a2584d259415608e
Source dataset
uspto-grants-1988_01
Patent number
US04720506

Reaction notes

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