Hydrazinecarboxylic acid, ethyl ester → ethyl 2[5-fluoro-2-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-ylidene]hydrazine carboxylate

HRID 22189

反応式

HRID 22189 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=O)[CH:6]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[CH2:5]2.[C:19]([O:23][CH2:24][CH3:25])(=[O:22])[NH:20][NH2:21]>CO.OS(O)(=O)=O>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[N:21][NH:20][C:19]([O:23][CH2:24][CH3:25])=[O:22])[CH:6]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[CH2:5]2

参加物

5

反応物 2

HCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 199754355-fluoro-2-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-one

生成物 1

HCID 56998361ethyl 2[5-fluoro-2-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-ylidene]hydrazine carboxylate収率 95%

試薬・触媒・溶媒 2

HCID 1118Sulfuric Acid触媒HCID 887Methanol溶媒

実験手順

To a mixture of 1.5 g of 5-fluoro-2-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-one (prepared by a procedure analogous to Example 1, Step B) and 0.63 g of ethyl carbazate in 20 ml of methanol was added 1 drop of conc. H2SO4 and the reaction was refluxed under nitrogen overnight. The reaction was then partitioned between ethyl acetate and 5% aqueous NaHCO3, the aqueous extracts were washed with ethyl acetate and the combined organic extracts were dried over MgSO4. Concentration of the organic extract afforded 1.9 g of a yellow oil, which was triturated with ether to afford 1.27 g of a white solid, m.p. 139°-141° C. 1H NMR (CDCl3) δ 1.26 (t, 3H), 2.91 (dd, 1H), 3.70 (dd, 1H), 4.2 (m, 3H), 6.9-7.3 (m, 6H), 7.52 (bs, 1H ), 7.93 (dd, 1H ).

後処理

  1. temperaturethe reaction was refluxed under nitrogen overnight
  2. customThe reaction was then partitioned between ethyl acetate and 5% aqueous NaHCO3
  3. washthe aqueous extracts were washed with ethyl acetate
  4. dry with materialthe combined organic extracts were dried over MgSO4
  5. extractionConcentration of the organic extract

出典と根拠

ORDレコード
ord-9e4ec8be14c54895b8dce5e69857e66d
出典データセット
uspto-grants-1995_06
特許番号
US05428027

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