Acetic Acid → HCID 10356293, compound

HRID 1656731Notes

Reaction equation

HRID 1656731 reaction equation
[F:1][C:2]1[C:11]([F:12])=[CH:10][C:9]2[C:13](=[O:20])[C:14]([C:16]([O:18]C)=[O:17])=[CH:15][N:7]3[C:8]=2[C:3]=1[CH2:4][CH2:5][N:6]3[CH3:21].Cl.C(O)(=O)C>O>[F:1][C:2]1[C:11]([F:12])=[CH:10][C:9]2[C:13](=[O:20])[C:14]([C:16]([OH:18])=[O:17])=[CH:15][N:7]3[C:8]=2[C:3]=1[CH2:4][CH2:5][N:6]3[CH3:21]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 19788691HCID 19788691, compound

Product 1

HCID 10356293HCID 10356293, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

29.1 g of methyl ester (6) obtained in Example 2 (1) was added to 80 ml of concentrated hydrochloric acid and 320 ml of acetic acid, and the solution was heated under reflux for 3.5 hours. After air-cooled, 500 ml of water was added to the solution, and the solid was filtered off and washed consecutively with water, ethanol and ether to obtain 23.2 g of crude solid. The obtained crude solid was recrystallized from ethanol and chloroform to obtain 21 g of subject compound (8) in a 80% yield. The result of the analysis of this compound was as follows.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 3.5 hours
  3. temperatureAfter air-cooled
  4. filtrationthe solid was filtered off
  5. washwashed consecutively with water, ethanol and ether
  6. customto obtain 23.2 g of crude solid
  7. customThe obtained crude solid
  8. customwas recrystallized from ethanol and chloroform

Sources & evidence

ORD record
ord-b4daa97119c54376807d2ccb513828ed
Source dataset
uspto-grants-1993_10
Patent number
US05254685

Reaction notes

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