Ammonia → 5,6-Bis(cyclohexylamino)-1H-isoindole-1,3(2H)-dione

HRID 2396049ノート

反応式

HRID 2396049 の反応式
C[O:2][C:3](=O)[C:4]1[C:5](=[CH:10][C:11]([NH:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[C:12]([NH:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:13]=1)[C:6](OC)=[O:7].[NH3:29].[Cl-].[Na+]>C(O)CO>[CH:15]1([NH:14][C:12]2[CH:13]=[C:4]3[C:3](=[O:2])[NH:29][C:6](=[O:7])[C:5]3=[CH:10][C:11]=2[NH:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1

参加物

5

反応物 3

HCID 222AmmoniaHCID 5234Sodium ChlorideHCID 10000342HCID 10000342、化合物

生成物 1

HCID 104500055,6-Bis(cyclohexylamino)-1H-isoindole-1,3(2H)-dione

試薬・触媒・溶媒 1

HCID 174Ethylene Glycol溶媒

実験手順

Analogously to Example 1, 194 mg (0.5 mmol) of 4,5-bis(cyclohexylamino)phthalic acid dimethyl ester in 15 ml of ethylene glycol are heated at 120°, ammonia gas being passed through the mixture, with stirring, for 12 hours. The reaction mixture is cooled, saturated with sodium chloride and extracted with ethyl acetate. The ethylacetate phases are washed in succession three times with water and once with saturated sodium chloride solution, dried with sodium sulfate and concentrated by evaporation. The evaporation residue is chromatographed onsilica gel with hexane/ethyl acetate 3:1 and the product fractions are combined and concentrated by evaporation, yielding the title compound in the form of orange crystals, m.p. 170°-175° C., FAB-MS: 342 [M+ +H].

後処理

  1. extractionextracted with ethyl acetate
  2. washThe ethylacetate phases are washed in succession three times with water and once with saturated sodium chloride solution
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated by evaporation
  5. customThe evaporation residue is chromatographed onsilica gel with hexane/ethyl acetate 3:1
  6. concentrationconcentrated by evaporation

出典と根拠

ORDレコード
ord-86a79904d4a64327947145a228f3808d
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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