Sodium Hydroxide → HCID 13023173, compound

HRID 1449237Notes

Reaction equation

HRID 1449237 reaction equation
[CH2:1]([N:8]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][C:24]([O:26]CC)=[O:25])[C:9]1[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:10]=1[Cl:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C.C1C=CC=CC=1>[CH2:1]([N:8]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][C:24]([OH:26])=[O:25])[C:9]1[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:10]=1[Cl:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 13023175HCID 13023175, compound

Product 1

HCID 13023173HCID 13023173, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

In a mixture of 50 ml of ethanol and 30 ml of benzene, 7.0 g (0.017 mole) of ethyl N-benzyl-o-(2,6-dichloroanilino)phenylacetate was dissolved and 31 ml of 2 N-NaOH aq. sol. was added and the mixture was stirred at about 80° C. for 9 hours. The reaction mixture was concentrated under reduced pressure and 70 ml of ether was added to the residue and the reaction product was extracted with 2 N-NaOH aq. sol. The pH of the water phase was adjusted with a dilute hydrochloric acid to 2.0 and the precipitate was extracted with ether and the ether phase was dried over anhydrous sodium sulfate and concentrated under a reduced pressure. The reaction product was recrystallized and 5.1 g of N-benzyl-o-(2,6-dichloroanilino)phenyl acetic acid was obtained as colorless crystals. Yield: 78%

Workup

  1. dissolutionwas dissolved
  2. concentrationThe reaction mixture was concentrated under reduced pressure and 70 ml of ether
  3. additionwas added to the residue
  4. extractionthe reaction product was extracted with 2 N-NaOH aq. sol. The pH of the water phase
  5. extractionthe precipitate was extracted with ether
  6. dry with materialthe ether phase was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under a reduced pressure
  8. customThe reaction product was recrystallized

Sources & evidence

ORD record
ord-7c4b12e51d484d2ab8cd4ff522907608
Source dataset
uspto-grants-1980_02
Patent number
US04189595

Reaction notes

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