Methanol → HCID 22485603, compound

HRID 2181322Notes

Reaction equation

HRID 2181322 reaction equation
[C:1]([C:4]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([C:12]2[CH:17]=[CH:16][C:15]([N:18]([CH3:42])[CH2:19][CH2:20][N:21]([C:23]3[CH:24]=[CH:25][C:26]([C:29]4[CH:34]=[C:33]([O:35][CH3:36])[C:32]([C:37](=[O:39])[CH3:38])=[C:31]([O:40][CH3:41])[CH:30]=4)=[N:27][CH:28]=3)[CH3:22])=[CH:14][N:13]=2)=[CH:6][C:5]=1[O:43][CH3:44])(=[O:3])[CH3:2].[CH3:45][S:46]([OH:49])(=[O:48])=[O:47].CO>C(Cl)(Cl)Cl>[CH3:45][S:46]([OH:49])(=[O:48])=[O:47].[CH3:45][S:46]([OH:49])(=[O:48])=[O:47].[C:37]([C:32]1[C:33]([O:35][CH3:36])=[CH:34][C:29]([C:26]2[CH:25]=[CH:24][C:23]([N:21]([CH3:22])[CH2:20][CH2:19][N:18]([C:15]3[CH:16]=[CH:17][C:12]([C:7]4[CH:6]=[C:5]([O:43][CH3:44])[C:4]([C:1](=[O:3])[CH3:2])=[C:9]([O:10][CH3:11])[CH:8]=4)=[N:13][CH:14]=3)[CH3:42])=[CH:28][N:27]=2)=[CH:30][C:31]=1[O:40][CH3:41])(=[O:39])[CH3:38]

Participants

5

Reactant 3

HCID 887MethanolHCID 6395Methanesulfonic AcidHCID 22485511HCID 22485511, compound

Product 1

HCID 22485603HCID 22485603, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of N,N′-bis[2-(4-acetyl-3,5-dimethoxyphenyl)-5-pyridyl]-N,N′-dimethylethylenediamine (76.4 mg, 0.128 mmol) in chloroform (5.0 mL) was added a 1.0 M solution of methanesulfonic acid in methanol (0.32 mL, 0.32 mmol), and the reaction mixture was concentrated under reduced pressure. Chloroform-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: 261.0-265.5° C.)(75.1 mg, yield: 74%).

Workup

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

Sources & evidence

ORD record
ord-2cb0607933d341e3894c4472e50c98a9
Source dataset
uspto-grants-2005_05
Patent number
US06890940B2

Reaction notes

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