Hippuric Acid → HCID 53890716, compound

HRID 426774Notes

Reaction equation

HRID 426774 reaction equation
C(=O)(O)[O-].[Na+].[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([S:15][C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)=[C:11]([CH:14]=1)[CH:12]=O.[C:21]([OH:33])(=[O:32])[CH2:22][NH:23][C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=O.C(OC(=O)C)(=O)C>C(O)C>[C:26]1([C:24]2[O:33][C:21](=[O:32])[C:22](=[CH:12][C:11]3[CH:14]=[C:7]([Cl:6])[CH:8]=[CH:9][C:10]=3[S:15][C:16]3[S:17][CH:18]=[CH:19][CH:20]=3)[N:23]=2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 464Hippuric AcidHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 20389867HCID 20389867, compound

Product 1

HCID 53890716HCID 53890716, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

8.4 g (0.1 mole) of sodium bicarbonate is added, with stirring, to the mixture of 25.5 g (0.1 mole) of 5-chloro-2-(2-thienylthio)-benzaldehyde and 17.9 g (0.1 mole) of hippuric acid in 34.7 g (0.34 mole) of acetic anhydride, and the reaction mixture is stirred at 90°-95° for two hours. It is thereupon cooled to 25°; to the thick crystal mass is added 300 ml of 50% ethanol, the solid substance is filtered off with suction and is washed with 150 ml of 50% ethanol. Drying in a vacuum chamber leaves 2-phenyl-4-[5-chloro-2-(2-thienylthio)-benzylidene]-2-oxazolin-5-one in the form of yellow crystals, m.p. 125°-127°.

Workup

  1. temperatureIt is thereupon cooled to 25°
  2. filtrationthe solid substance is filtered off with suction
  3. washis washed with 150 ml of 50% ethanol
  4. customDrying in a vacuum chamber

Sources & evidence

ORD record
ord-a9da4f6bf4a04353abe4171d89e9bcd1
Source dataset
uspto-grants-1979_10
Patent number
US04171366

Reaction notes

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