Acetic Acid → Ethyl 2-(4-carboxybenzamido)-4-propionamidobenzoate

HRID 27468Notes

Reaction equation

HRID 27468 reaction equation
[C:1]([NH:5][C:6]1[CH:25]=[CH:24][C:9]2[C:10](=[O:23])[O:11][C:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([OH:22])=[O:21])=[CH:16][CH:15]=3)=[N:13][C:8]=2[CH:7]=1)(=[O:4])[CH2:2][CH3:3].[CH2:26]([OH:28])[CH3:27].C(N(CC)CC)C.C(O)(=O)C>O>[C:20]([C:17]1[CH:16]=[CH:15][C:14]([C:12]([NH:13][C:8]2[CH:7]=[C:6]([NH:5][C:1](=[O:4])[CH2:2][CH3:3])[CH:25]=[CH:24][C:9]=2[C:10]([O:28][CH2:26][CH3:27])=[O:23])=[O:11])=[CH:19][CH:18]=1)([OH:22])=[O:21]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 8471TriethylamineHCID 130200727-(propionamido)-2-(4-carboxyphenyl)-4H-3,1-benzoxazine-4-one

Product 1

HCID 6918053Ethyl 2-(4-carboxybenzamido)-4-propionamidobenzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 12 g of 7-(propionamido)-2-(4-carboxyphenyl)-4H-3,1-benzoxazine-4-one, 120 ml of absolute ethanol and 9 ml of triethylamine was heated under reflux for a period of 8 hours. After being allowed to cool, the mixture was added with 9 ml of acetic acid and 500 ml of water, the precipitating crystal was filtered, and recrystallized from a solvent mixture of ethanol and water to yield 10 g of ethyl 2-(4-carboxybenzamido)-4-propionamidobenzoate having a melting point in the range of from 246° to 248° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for a period of 8 hours
  3. temperatureto cool
  4. filtrationthe precipitating crystal was filtered
  5. customrecrystallized from a solvent mixture of ethanol and water

Sources & evidence

ORD record
ord-8096721ce39442b48494be0e51c64762
Source dataset
uspto-grants-1980_09
Patent number
US04221814

Reaction notes

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