Methanesulfonic Acid → HCID 22485576, compound

HRID 2181306Notes

Reaction equation

HRID 2181306 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[C:11]1[CH:16]=[CH:15][C:14]([N:17]([CH3:38])[CH2:18][CH2:19][N:20]([C:22]2[CH:23]=[CH:24][C:25]([C:28]3[C:33]([O:34][CH3:35])=[CH:32][CH:31]=[CH:30][C:29]=3[O:36][CH3:37])=[N:26][CH:27]=2)[CH3:21])=[CH:13][N:12]=1.[CH3:39][S:40]([OH:43])(=[O:42])=[O:41]>CO.C(Cl)(Cl)Cl>[CH3:39][S:40]([OH:43])(=[O:42])=[O:41].[CH3:39][S:40]([OH:43])(=[O:42])=[O:41].[CH3:35][O:34][C:33]1[CH:32]=[CH:31][CH:30]=[C:29]([O:36][CH3:37])[C:28]=1[C:25]1[CH:24]=[CH:23][C:22]([N:20]([CH3:21])[CH2:19][CH2:18][N:17]([C:14]2[CH:15]=[CH:16][C:11]([C:4]3[C:5]([O:9][CH3:10])=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])=[N:12][CH:13]=2)[CH3:38])=[CH:27][N:26]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 22485577HCID 22485577, compound

Product 1

HCID 22485576HCID 22485576, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

To a solution of N,N′-bis[2-(2,6-dimethoxyphenyl)-5-pyridyl]-N,N′-dimethylethylenediamine (72.3 mg, 0.141 mmol) in methanol-chloroform (9:1, 10 mL) was added a 1.0 M aqueous methanesulfonic acid solution (0.35 mL, 0.35 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 ethanol-diethyl ether to provide the title compound as a pale yellow crystalline powder (melting point: 243.0-245.0° C. )(94.1 mg, yield: 95%).

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 ethanol-diethyl ether

Sources & evidence

ORD record
ord-ac9b682967f24efd83c6bf77f47f4f98
Source dataset
uspto-grants-2005_05
Patent number
US06890940B2

Reaction notes

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