HCID 57287670, compound → Eltenac

HRID 1680165Notes

Reaction equation

HRID 1680165 reaction equation
C([O:8][C:9](=[O:25])[CH2:10][C:11]1[C:15]([NH:16][C:17]2[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:24])=[CH:14][S:13][CH:12]=1)C1C=CC=CC=1.[H][H]>C(OCC)(=O)C.C(O)(=O)C.[Pd]>[Cl:24][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]([Cl:23])[C:17]=1[NH:16][C:15]1[C:11]([CH2:10][C:9]([OH:25])=[O:8])=[CH:12][S:13][CH:14]=1

Participants

6

Reactant 2

HCID 57287670HCID 57287670, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 51717Eltenac

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

393 mg (1 mmole) of 4-(2,6-dichloroanilino)-3-thiophenacetic acid benzyl ester are subjected to hydrogenolysis (in a mixture of 100 ml of ethyl acetate and 10 ml of glacial acetic acid in a circulatory hydrogenation apparatus in the presence of 50 mg of 10 percent strength palladium-on-active charcoal at room temperature and under atmospheric pressure) until the theoretical amount of hydrogen has been taken up. The catalyst is filtered off, the filtrate is concentrated in vacuo, and the residue is dissolved in 1 N sodium hydroxide solution. The aqueous solution is extracted with toluene, and the product phase is acidified with 1 N hydrochloric acid and extracted again with toluene. The organic phase is dried and concentrated. 4-(2,6-Dichloroanilino)-3-thiophenacetic acid (m. 179° to 180°) is obtained.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated in vacuo
  3. dissolutionthe residue is dissolved in 1 N sodium hydroxide solution
  4. extractionThe aqueous solution is extracted with toluene
  5. extractionextracted again with toluene
  6. customThe organic phase is dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4555f856d4334156aca82e16b1baa2ab
Source dataset
uspto-grants-1981_06
Patent number
US04272507

Reaction notes

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