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

HRID 375105

반응식

HRID 375105 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-653defac515a43f8b413b91ec0076dd6
출처 데이터셋
uspto-grants-1996_01
특허 번호
US05484792

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