Methanol → HCID 22485625, compound

HRID 2181305Notes

Reaction equation

HRID 2181305 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][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[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH3:35])[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].[CH3:37][O:36][C:29]1[C:30]([O:34][CH3:35])=[CH:31][CH:32]=[CH:33][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[CH:5]=[CH:6][CH:7]=[C:8]([O:9][CH3:10])[C:3]=3[O:2][CH3:1])=[N:12][CH:13]=2)[CH3:38])=[CH:27][N:26]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6395Methanesulfonic AcidHCID 22485493HCID 22485493, compound

Product 1

HCID 22485625HCID 22485625, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of N,N′-bis[2-(2,3-dimethoxyphenyl)-5-pyridyl]-N,N′-dimethylethylenediamine (33.0 mg, 0.0641 mmol) in chloroform (3.0 mL) was added a 1.0 M solution of methanesulfonic acid in methanol (0.13 mL, 0.13 mmol), and the reaction mixture was concentrated under reduced pressure. Methanol-diethyl ether was added to the residue and the resulting precipitate was collected by filtration to yield the title compound as a yellow crystalline powder (melting point: 191.5-194.5° C.)(39.5 mg, yield: 87%).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionMethanol-diethyl ether was added to the residue
  3. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-22f911e8cc42419ab67ae9572654c675
Source dataset
uspto-grants-2005_05
Patent number
US06890940B2

Reaction notes

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