1,3-Cyclohexanedione → 9-(4-Phenylsulfonylphenyl)-3,4,6,7,9,10-hexahydro-1,8-(2H,5H)acridinedione

HRID 375105ノート

反応式

HRID 375105 の反応式
[C:1]1([S:7]([C:10]2[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18]1(=[O:25])[CH2:23][CH2:22][CH2:21][C:20](=O)[CH2:19]1.[C:26]([O-:29])(=O)[CH3:27].[NH4+:30]>C(O)C>[C:1]1([S:7]([C:10]2[CH:17]=[CH:16][C:13]([CH:14]3[C:19]4[C:18](=[O:25])[CH2:23][CH2:22][CH2:21][C:20]=4[NH:30][C:1]4[CH2:2][CH2:3][CH2:27][C:26](=[O:29])[C:6]3=4)=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

5

反応物 3

HCID 104341,3-CyclohexanedioneHCID 517165Ammonium AcetateHCID 144174774-(Benzenesulfonyl)benzaldehyde

生成物 1

HCID 189943109-(4-Phenylsulfonylphenyl)-3,4,6,7,9,10-hexahydro-1,8-(2H,5H)acridinedione

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A stirred mixture of 4-phenylsulfonylbenzaldehyde (1.23 g), 1,3-cyclohexanedione (1.12 g), ammonium acetate (0.58 g) and ethanol (10 mL) was refluxed for 4 hours. The mixture was cooled and the light yellow crystals were collected, washed with water and dried in vacuo. A second crop obtained, by treatment of the liquors with water, was added to the dried solid and the total material was chromatographed with ether:methylene chloride as the eluent (20:80) followed by methanol:dichloromethane (10:90). Evaporation and recrystallization from ethanol:hexane yielded the title compound as a hemihydrate (1.10 g) as a pale yellow solid; mp 260° C.; NMR: 1.74-1.93 (m,4), 2.11-2.26 (m,4), 2.43-2.57 (m,4), 4.94 (s,1), 7.38 (d,2, J=8.3), 7.56-7.69 (m,3,), 7.77 (d,2, J=8.2), 7.93 (dd,2, J=8.3, 1.4), 9.53 (s,1,); MS: m/z=434(M+1 ). Found for C25H23NO4S.0.5 H2O: C, 67.88; H,5.37; N, 3.14.

後処理

  1. temperaturewas refluxed for 4 hours
  2. temperatureThe mixture was cooled
  3. customthe light yellow crystals were collected
  4. washwashed with water
  5. customdried in vacuo
  6. customA second crop obtained, by treatment of the liquors with water
  7. additionwas added to the dried solid
  8. customthe total material was chromatographed with ether
  9. customEvaporation and recrystallization from ethanol

出典と根拠

ORDレコード
ord-653defac515a43f8b413b91ec0076dd6
出典データセット
uspto-grants-1996_01
特許番号
US05484792

反応ノート

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