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Phosphorus oxychloride → (+/-)-cis-8,9-Dimethoxy-6-(4-p-toluenesulfonamidophenyl)-1,2,3,4,4a,10b-hexahydrophenanthridine

HRID 365401
Notes
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Reaction equation

HRID 365401 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]2[NH:17][C:18](=O)[C:19]2[CH:24]=[CH:23][C:22]([NH:25][S:26]([C:29]3[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=3)(=[O:28])=[O:27])=[CH:21][CH:20]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].P(Cl)(Cl)(Cl)=O.C(=O)([O-])O.[Na+]>C(#N)C>[CH3:10][O:9][C:8]1[CH:7]=[C:6]2[C:5](=[CH:4][C:3]=1[O:2][CH3:1])[C@H:11]1[C@H:12]([CH2:13][CH2:14][CH2:15][CH2:16]1)[N:17]=[C:18]2[C:19]1[CH:20]=[CH:21][C:22]([NH:25][S:26]([C:29]2[CH:30]=[CH:31][C:32]([CH3:35])=[CH:33][CH:34]=2)(=[O:27])=[O:28])=[CH:23][CH:24]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 15410434(+/-)-cis-N-[2-(3,4-dimethoxyphenyl)cyclohexyl]-4-p-toluenesulfonamidobenzamide

Product 1

HCID 15410435(+/-)-cis-8,9-Dimethoxy-6-(4-p-toluenesulfonamidophenyl)-1,2,3,4,4a,10b-hexahydrophenanthridine

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Procedure

3.5 g of (+/-)-cis-N-[2-(3,4-dimethoxyphenyl)cyclohexyl]-4-p-toluenesulfonamidobenzamide are dissolved in 100 ml of acetonitrile and 1.0 ml of phosphorus oxychloride and the solution is stirred at 50° C. for 8 h. The reaction mixture is added to 100 ml of saturated sodium hydrogencarbonate solution and extracted with ethyl acetate. The organic phase is washed with sodium hydrogencarbonate solution and water, dried using sodium sulfate and concentrated. The residue is recrystallized from ethanol. 1.8 g (53.2% of theory) of the title compound of melting point: 122° C. (decomposition) are obtained.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase is washed with sodium hydrogencarbonate solution and water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-76cbdf80abef42d792ac28d630e84d14
Source dataset
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06127378

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes