Methanesulfonic Acid → HCID 22485524, compound

HRID 2181307Notes

Reaction equation

HRID 2181307 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:18]=[CH:17][C:16]([N:19]([CH3:42])[CH2:20][CH2:21][N:22]([C:24]3[CH:25]=[CH:26][C:27]([C:30]4[CH:35]=[C:34]([O:36][CH3:37])[C:33]([O:38][CH3:39])=[C:32]([O:40][CH3:41])[CH:31]=4)=[N:28][CH:29]=3)[CH3:23])=[CH:15][N:14]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[CH3:43][S:44]([OH:47])(=[O:46])=[O:45]>CO.C(Cl)Cl>[CH3:43][S:44]([OH:47])(=[O:46])=[O:45].[CH3:43][S:44]([OH:47])(=[O:46])=[O:45].[CH3:37][O:36][C:34]1[CH:35]=[C:30]([C:27]2[CH:26]=[CH:25][C:24]([N:22]([CH3:23])[CH2:21][CH2:20][N:19]([C:16]3[CH:17]=[CH:18][C:13]([C:5]4[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=4)=[N:14][CH:15]=3)[CH3:42])=[CH:29][N:28]=2)[CH:31]=[C:32]([O:40][CH3:41])[C:33]=1[O:38][CH3:39]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 22485518HCID 22485518, compound

Product 1

HCID 22485524HCID 22485524, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of N,N′-bis[2-(3,4,5-trimethoxyphenyl)-5-pyridyl]-N,N′-dimethylethylenediamine (140.0 mg, 0.240 mmol) in methanol-methylene chloride (1:1, 6.0 mL) was added a 1.0 M aqueous methanesulfonic acid (0.48 mL, 0.48 mmol) and the reaction mixture was concentrated under reduced pressure. Ethanol (5.0 mL) was added to the residue and the mixture was concentrated under reduced pressure. The residue was recrystallized from methanol-methylene chloride-diethyl ether to provide the title compound as a yellow crystalline powder (melting point: 247.0-249.0° C. )(140.0 mg, yield: 76%).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionEthanol (5.0 mL) was added to the residue
  3. concentrationthe mixture was concentrated under reduced pressure
  4. customThe residue was recrystallized from methanol-methylene chloride-diethyl ether

Sources & evidence

ORD record
ord-906d49d78d16400bb49fc86e4c8a4198
Source dataset
uspto-grants-2005_05
Patent number
US06890940B2

Reaction notes

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