Acetic Anhydride → HCID 15871313, Verbindung

HRID 727389

Reaktionsgleichung

Reaktionsgleichung von HRID 727389
CC1C=CC(C)=CC=1C(CC#N)=O.COC(OC)(OC)CCC.C(OC(=O)C)(=O)C.[C:31]([C:33]([C:40](=[O:49])[C:41]1[CH:46]=[C:45]([CH3:47])[CH:44]=[CH:43][C:42]=1[CH3:48])=[CH:34][CH:35](OC)[CH2:36][CH3:37])#[N:32].C(N(CC)CC)C.[Cl:57][C:58]1[CH:63]=[C:62]([C:64]([F:67])([F:66])[F:65])[CH:61]=[C:60]([Cl:68])[C:59]=1[NH:69][NH2:70]>C(OCC)(=O)C>[NH2:32][C:31]1[N:69]([C:59]2[C:60]([Cl:68])=[CH:61][C:62]([C:64]([F:65])([F:66])[F:67])=[CH:63][C:58]=2[Cl:57])[N:70]=[C:34]([CH2:35][CH2:36][CH3:37])[C:33]=1[C:40](=[O:49])[C:41]1[CH:46]=[C:45]([CH3:47])[CH:44]=[CH:43][C:42]=1[CH3:48]

Komponenten

8

Edukt 6

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 1235121,1,1-TrimethoxybutaneHCID 688223[2,6-Dichloro-4-(trifluoromethyl)phenyl]hydrazineHCID 158952642,5-DimethylbenzoylacetonitrileHCID 536488461-Cyano-1-(2,5-dimethylbenzoyl)-3-methoxy-1-pentene

Produkt 1

HCID 15871313HCID 15871313, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 0.52 g (3.0 mmol) of 2,5-dimethylbenzoylacetonitrile, 0.45 g (3.0 mmol) of trimethylorthobutyrate and 0.632 g (0.58 mL, 6.2 mmol) of acetic anhydride in 5.0 mL of ethyl acetate was refluxed overnight and then cooled. The solvents were removed in vacuo and the residues were dissolved in 10 mL of ethanol. One-half of this solution, containing 1.5 mmol of 1-cyano-1-(2,5-dimethylbenzoyl)-3-methoxy-1-pentene was mixed with 0.7 mL (0.51 g, 5.0 mmol) of triethylamine and 0.37 g (1.50 mmol) of 2,6-dichloro-4-trifluoromethylphenylhydrazine and refluxed for 2.5 hours. The reaction mixture was cooled and partitioned between dilute hydrogen chloride and ethyl acetate. The organic phase was washed with water and then dried with brine and with magnesium sulfate. The solvent was evaporated to give an oil which was chromatographed on silica gel by the flash method eluting with 4:1 hexane/ethyl acetate to give the title compound as an amorphous foam. Anal. Calcd. for C22H20ON3CL2F3, 469.0935. Found: 469.0889.

Aufarbeitung

  1. temperaturecooled
  2. customThe solvents were removed in vacuo
  3. dissolutionthe residues were dissolved in 10 mL of ethanol
  4. temperaturerefluxed for 2.5 hours
  5. temperatureThe reaction mixture was cooled
  6. custompartitioned between dilute hydrogen chloride and ethyl acetate
  7. washThe organic phase was washed with water
  8. dry with materialdried with brine and with magnesium sulfate
  9. customThe solvent was evaporated
  10. customto give an oil which
  11. customwas chromatographed on silica gel by the flash method
  12. washeluting with 4:1 hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-fbc3da8862f144fd81839583d69cc429
Quelldatensatz
uspto-grants-1998_01
Patentnummer
US05712303

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