Ethyl Acetate → HCID 135979303, compound

HRID 1586096Notes

Reaction equation

HRID 1586096 reaction equation
[CH:1]1([CH2:4][O:5][N:6]=[C:7]([NH2:19])[C:8]2[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:11]=[CH:10][C:9]=2F)[CH2:3][CH2:2]1.[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29](Cl)=[O:30])=[CH:24][CH:23]=1.C(OCC)(=O)C>C1C=CC=CC=1>[CH:1]1([CH2:4][O:5][N:6]=[C:7]([NH:19][C:29](=[O:30])[CH2:28][C:25]2[CH:26]=[CH:27][C:22]([O:21][CH3:20])=[CH:23][CH:24]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=2[C:14]([F:17])([F:16])[F:15])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 27346884-Methoxyphenylacetyl chlorideHCID 54459581HCID 54459581, compound

Product 1

HCID 135979303HCID 135979303, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In 80 ml of benzene was dissolved 10.4 g of N'-cyclopropylmethyloxy-2-fluoro-6-trifluoromethylbenzamidine, and to the solution was added 8.9 g of 4-methoxyphenylacetylchloride. The solution was heated under refluxing for 3 hours. After cooling, ethyl acetate was added to the solution, followed by washing with water and drying over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure and the residue obtained in crystal was washed with a mixed solvent hexane and ether to thereby obtain 13.7 g of crude crystal. The crystal was then re-crystallized in hexane, thereby affording 11.5 g of the objective compound.m.p. 88-90° C.

Workup

  1. temperatureThe solution was heated
  2. temperatureunder refluxing for 3 hours
  3. temperatureAfter cooling
  4. washby washing with water
  5. dry with materialdrying over anhydrous magnesium sulfate
  6. concentrationThe organic layer was concentrated under reduced pressure
  7. customthe residue obtained in crystal
  8. washwas washed with a mixed solvent hexane and ether
  9. customto thereby obtain 13.7 g of crude crystal
  10. customThe crystal was then re-crystallized in hexane

Sources & evidence

ORD record
ord-0218c766caab498592607a8b1d16aace
Source dataset
uspto-grants-1999_08
Patent number
US05942538

Reaction notes

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