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

HRID 375105Notes

Reaction equation

HRID 375105 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-653defac515a43f8b413b91ec0076dd6
Source dataset
uspto-grants-1996_01
Patent number
US05484792

Reaction notes

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