Carbon Tetrachloride → HCID 66607261, compound

HRID 71105Notes

Reaction equation

HRID 71105 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([NH:12][NH:13][C:14](=O)[C:15]2[CH:20]=[CH:19][C:18]([C:21]3[O:25][C:24]([CH3:26])=[N:23][CH:22]=3)=[C:17]([O:27][CH3:28])[CH:16]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[F:8].C(Cl)(Cl)(Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[F:8])[CH2:9][C:10]1[O:11][C:14]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[O:25][C:24]([CH3:26])=[N:23][CH:22]=3)=[C:17]([O:27][CH3:28])[CH:16]=2)=[N:13][N:12]=1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 66607891N'-[(3,4-difluorophenyl)acetyl]-3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)benzohydrazide

Product 1

HCID 66607261HCID 66607261, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of N′-[(3,4-difluorophenyl)acetyl]-3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)benzohydrazide (4.69 g), carbon tetrachloride (2.24 mL) and triphenylphosphine (12.3 g) in acetonitrile (117 mL) was stirred at 80° C. for 2 hr. The mixture was allowed to cool to room temperature, the precipitate was filtered off, and the filtrate was concentrated. Water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate). Ethyl acetate was added to the obtained crude product, the precipitate was filtered off, and the filtrate was concentrated. Acetonitrile was added to the obtained residue, and the resultant precipitate was collected by filtration to give the title compound (2.41 g).

Workup

  1. temperatureto cool to room temperature
  2. filtrationthe precipitate was filtered off
  3. concentrationthe filtrate was concentrated
  4. additionWater was added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialThe extract was dried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate)
  9. additionEthyl acetate was added to the
  10. customobtained crude product
  11. filtrationthe precipitate was filtered off
  12. concentrationthe filtrate was concentrated
  13. additionAcetonitrile was added to the obtained residue
  14. filtrationthe resultant precipitate was collected by filtration

Sources & evidence

ORD record
ord-79c8850a2800400a9fb5762436a9d847
Source dataset
uspto-grants-2014_09
Patent number
US08822699B2

Reaction notes

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