Methanesulfonic Acid → HCID 22485607, compound

HRID 2181317Notes

Reaction equation

HRID 2181317 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[CH:17]=[CH:16][C:15]([N:18]([CH3:40])[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]([CH3:37])=[C:31]([O:38][CH3:39])[CH:30]=4)=[N:27][CH:28]=3)[CH3:22])=[CH:14][N:13]=2)[CH:6]=[C:7]([O:10][CH3:11])[C:8]=1[CH3:9].[CH3:41][S:42]([OH:45])(=[O:44])=[O:43]>CO>[CH3:41][S:42]([OH:45])(=[O:44])=[O:43].[CH3:41][S:42]([OH:45])(=[O:44])=[O:43].[CH3:36][O:35][C:33]1[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:5]4[CH:4]=[C:3]([O:2][CH3:1])[C:8]([CH3:9])=[C:7]([O:10][CH3:11])[CH:6]=4)=[N:13][CH:14]=3)[CH3:40])=[CH:28][N:27]=2)[CH:30]=[C:31]([O:38][CH3:39])[C:32]=1[CH3:37]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 22485469HCID 22485469, compound

Product 1

HCID 22485607HCID 22485607, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N,N′-bis[2-(3,5-dimethoxy-4-methylphenyl)-5-pyridyl]-N,N′-dimethylethylenediamine (37.0 mg, 0.070 mmol) in methanol (2.0 mL) was added a 1.0 M aqueous methanesulfonic acid (0.15 mL, 0.15 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-chloroform to yield the title compound as a yellow crystalline powder (melting point: 272.0-274.0° C.)(22.0 mg, yield: 44%).

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-chloroform

Sources & evidence

ORD record
ord-cbf1e581ab29411aa248510a37ba3580
Source dataset
uspto-grants-2005_05
Patent number
US06890940B2

Reaction notes

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