4-Toluenesulfonyl chloride → (+/-)-cis-8,9-Dimethoxy-6-[4-bis(p-toluenesulfonyl)aminophenyl]-1,2,3,4,4a,10b-hexahydrophenanthridine

HRID 365406Notes

Reaction equation

HRID 365406 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][C:16]=1[O:17][CH3:18])[C@H:13]1[C@H:8]([CH2:9][CH2:10][CH2:11][CH2:12]1)[N:7]=[C:6]2[C:19]1[CH:24]=[CH:23][C:22]([NH:25][S:26]([C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=2)(=[O:28])=[O:27])=[CH:21][CH:20]=1.[C:36]1([CH3:46])[CH:41]=[CH:40][C:39]([S:42](Cl)(=[O:44])=[O:43])=[CH:38][CH:37]=1.[H-].[Na+]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][C:16]=1[O:17][CH3:18])[C@H:13]1[C@H:8]([CH2:9][CH2:10][CH2:11][CH2:12]1)[N:7]=[C:6]2[C:19]1[CH:24]=[CH:23][C:22]([N:25]([S:42]([C:39]2[CH:40]=[CH:41][C:36]([CH3:46])=[CH:37][CH:38]=2)(=[O:44])=[O:43])[S:26]([C:29]2[CH:30]=[CH:31][C:32]([CH3:35])=[CH:33][CH:34]=2)(=[O:27])=[O:28])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 15410435(+/-)-cis-8,9-Dimethoxy-6-(4-p-toluenesulfonamidophenyl)-1,2,3,4,4a,10b-hexahydrophenanthridine

Product 1

HCID 86755880(+/-)-cis-8,9-Dimethoxy-6-[4-bis(p-toluenesulfonyl)aminophenyl]-1,2,3,4,4a,10b-hexahydrophenanthridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

2.0 g of (+/-)-cis-8,9-dimethoxy-6-(4-p-toluenesulfonamidophenyl)-1,2,3,4,4a,10b-hexahydrophenanthridine in 5 ml of dimethylformamide and then 1.0 g of p-toluenesulfonyl chloride in 5 ml of dimethylformamide are added dropwise to a suspension of 200 mg of 80% strength sodium hydride in 20 ml of dimethylformamide. After stirring at RT for 2 h, the mixture is added to ice-water and extracted with ethyl acetate/diethyl ether in the ratio 1:1. After drying and concentration of the organic phase, the residue is chromatographed on silica gel using a mixture of ethyl acetate/petroleum ether in the ratio 4:1. After concentration of the corresponding eluate fractions, the title compound of m.p. 120-130° C. is obtained.

Workup

  1. extractionextracted with ethyl acetate/diethyl ether in the ratio 1:1
  2. customAfter drying
  3. customconcentration of the organic phase, the residue is chromatographed on silica gel using
  4. additiona mixture of ethyl acetate/petroleum ether in the ratio 4:1

Sources & evidence

ORD record
ord-5b08debcd55a4418b958727c376df586
Source dataset
uspto-grants-2000_10
Patent number
US06127378

Reaction notes

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