4-Methoxybenzenesulfonyl chloride → HCID 22482377, compound

HRID 2181799Notes

Reaction equation

HRID 2181799 reaction equation
[CH2:1]([CH:3]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[NH:4]1)[CH3:2].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>N1C=CC=CC=1>[CH2:1]([CH:3]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]1[S:25]([C:22]1[CH:21]=[CH:20][C:19]([O:18][CH3:17])=[CH:24][CH:23]=1)(=[O:27])=[O:26])[CH3:2]

Participants

4

Reactant 2

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 22482300HCID 22482300, compound

Product 1

HCID 22482377HCID 22482377, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 6-ethyl-5,6-dihydrophenanthridine (14 g, 69.2 mmol) and 4-methoxybenzenesulfonyl chloride (17.2 g, 83 mmol) in pyridine (100 ml) was heated at 80° C. overnight. The solvent was evaporated in vacuo; and the crude product was purified by preparative column chromatography on silica gel, eluting with a gradient and mixture of dichloromethane-hexane (50:50 to 100:0). After evaporation of the solvent, the residue was crystallized from diethyl ether, yielding the title compound (22.8 g, 60.1 mmol, 87%) as a colorless, crystalline solid, which was characterized by LCMS (ES+, FA, CV=5) and 1H NMR.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customand the crude product was purified by preparative column chromatography on silica gel
  3. washeluting with a gradient and mixture of dichloromethane-hexane (50:50 to 100:0)
  4. customAfter evaporation of the solvent
  5. customthe residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-be6c317a515148e1a3b02c7fc72589f8
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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