Acetic Acid → HCID 10320817、化合物

HRID 2396061ノート

反応式

HRID 2396061 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH2:10][C:9](O[Si](C)(C)C)=[C:8](O[Si](C)(C)C)[CH2:7][C:6]=1[C:21]([O:23][CH3:24])=[O:22])=[O:4].[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([NH2:33])=[CH:29][CH:28]=1.[NH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[C:41](O)(=[O:43])C>>[CH3:1][O:2][C:3](=[O:4])[C:5]1[C:6](=[CH:7][C:8]([NH:34][C:35]2[CH:40]=[CH:39][C:38]([O:43][CH3:41])=[CH:37][CH:36]=2)=[C:9]([NH:33][C:30]2[CH:31]=[CH:32][C:27]([O:26][CH3:25])=[CH:28][CH:29]=2)[CH:10]=1)[C:21]([O:23][CH3:24])=[O:22]

参加物

5

反応物 4

HCID 176Acetic AcidHCID 6115AnilineHCID 7732P-AnisidineHCID 100221904,5-Bis(trimethylsilyloxy)cyclohexa-1,4-diene-1,2-dicarboxylic acid dimethyl ester

生成物 1

HCID 10320817HCID 10320817、化合物

実験手順

A solution of 4.8 g (12 mmol) 4,5-Bis(trimethylsilyloxy)-cyclohexa-1,4-diene-1,2-dicarboxylic acid dimethyl ester (Example 1a), 2.6 g (24 mmol) p-anisidine and 2.2 ml (24 mmol) aniline in 48 ml of glacial acetic acid is boiled under reflux for 2hours. The reaction mixture is cooled, the solvent is evaporated and the dark-brown residue is dissolved in ethyl acetate and the solution is washed in succession with 40 ml of 1N HCl, 100 ml of saturated NaHCO3and twice with water, dried with magnesium sulfate and concentrated by evaporation. The evaporation residue is chromatographed on silica gel withethyl acetate/hexane 1:3 and the product fractions are concentrated by evaporation. This way, in the first product fractions 4,5-bis-(4-methoxy-anilino)-phthalic acid dimethyl ester is obtained in the form of a yellow foam: FAB-MS: 437 [M+ +H]. The evaporation residue of the product fractions following thereafter is recrystallized, and 4-anilino-5-(4-methoxy-anilino)-phthalic acid dimethyl ester is obtained in the form of yellow crystals, m.p. 122°-4° C., FAB-MS: 407 [M+ +H].

後処理

  1. temperatureunder reflux for 2hours
  2. temperatureThe reaction mixture is cooled
  3. customthe solvent is evaporated
  4. dissolutionthe dark-brown residue is dissolved in ethyl acetate
  5. washthe solution is washed in succession with 40 ml of 1N HCl, 100 ml of saturated NaHCO3and twice with water
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated by evaporation
  8. customThe evaporation residue is chromatographed on silica gel withethyl acetate/hexane 1:3
  9. concentrationthe product fractions are concentrated by evaporation

出典と根拠

ORDレコード
ord-77722b88c8c2460ca96a30ca52c475cd
出典データセット
uspto-grants-1996_02
特許番号
US05491144

反応ノート

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