Acetic Anhydride → 5-Amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-(2,5-dimethylbenzoyl)-3-ethoxypyrazole

HRID 727397

反応式

HRID 727397 の反応式
[CH3:1][C:2]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:3]=1[C:4]([CH2:6][C:7]#[N:8])=[O:5].C(O[C:17]([O:24][CH2:25][CH3:26])(OCC)OCC)C.C(OC(=O)C)(=O)C.[Cl:34][C:35]1[CH:40]=[C:39]([C:41]([F:44])([F:43])[F:42])[CH:38]=[C:37]([Cl:45])[C:36]=1[NH:46][NH2:47].C(N(CC)CC)C>CCOC(C)=O.O>[NH2:8][C:7]1[N:46]([C:36]2[C:37]([Cl:45])=[CH:38][C:39]([C:41]([F:42])([F:43])[F:44])=[CH:40][C:35]=2[Cl:34])[N:47]=[C:17]([O:24][CH2:25][CH3:26])[C:6]=1[C:4](=[O:5])[C:3]1[CH:9]=[C:10]([CH3:13])[CH:11]=[CH:12][C:2]=1[CH3:1]

参加物

8

反応物 5

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 66213Tetraethyl orthocarbonateHCID 688223[2,6-Dichloro-4-(trifluoromethyl)phenyl]hydrazineHCID 158952642,5-Dimethylbenzoylacetonitrile

生成物 1

HCID 129721435-Amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-(2,5-dimethylbenzoyl)-3-ethoxypyrazole

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 0.26 g (1.5 mmol) of 2,5-dimethylbenzoylacetonitrile, 0.34 mL (0.31 g, 1.60 mmol) of tetraethylorthocarbonate and 0.30 mL (0.33 g, 3.20 mmol) of acetic anhydride in 10 mL of EtOAc was refluxed overnight. The solvent was evaporated and 10 mL of absolute ethanol was added and then stripped. The residues were dissolved in 10 mL of ethanol, 368 mg (1.5 mmol) of 2,6-dichloro-4-trifluoromethylphenylhydrazine and 0.7 mL (0.51 g, 5.0 mmol) of triethylamine were added, and the mixture was refluxed for 90 minutes. The mixture was poured into water, extracted with EtOAc and the organic extracts were washed with dilute HCl and brine, and dried over MgSO4. Evaporation gave a gum which was chromatographed on silica gel with 4:1 hexane/EtOAc to give the title product which crystallized from pentane, 15 mg (2%), m.p. 99°-101° C.

後処理

  1. customThe solvent was evaporated
  2. addition10 mL of absolute ethanol was added
  3. dissolutionThe residues were dissolved in 10 mL of ethanol
  4. temperaturethe mixture was refluxed for 90 minutes
  5. extractionextracted with EtOAc
  6. washthe organic extracts were washed with dilute HCl and brine
  7. dry with materialdried over MgSO4
  8. customEvaporation
  9. customgave a gum which
  10. customwas chromatographed on silica gel with 4:1 hexane/EtOAc

出典と根拠

ORDレコード
ord-89124b2ae7844187a54394383f88df9e
出典データセット
uspto-grants-1998_01
特許番号
US05712303

関連ノート

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