Acetic Anhydride → HCID 15871313、化合物

HRID 612982

反応式

HRID 612982 の反応式
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]

参加物

8

反応物 6

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 1235121,1,1-TrimethoxybutaneHCID 688223[2,6-Dichloro-4-(trifluoromethyl)phenyl]hydrazineHCID 158952643-(2,5-Dimethylphenyl)-3-oxopropanenitrileHCID 536488461-Cyano-1-(2,5-dimethylbenzoyl)-3-methoxy-1-pentene

生成物 1

HCID 15871313HCID 15871313、化合物

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9246fe02c12d4ba2b785b0bc098d3e87
出典データセット
uspto-grants-1999_12
特許番号
US06005109

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