Methanesulfonic Acid → HCID 22485619, compound

HRID 2181308Notes

Reaction equation

HRID 2181308 reaction equation
[CH2:1]([O:3][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]([O:37][CH2:38][CH3:39])=[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])[CH3:2].[CH3:45][S:46]([OH:49])(=[O:48])=[O:47]>CO>[CH3:45][S:46]([OH:49])(=[O:48])=[O:47].[CH3:45][S:46]([OH:49])(=[O:48])=[O:47].[CH2:38]([O:37][C:32]1[C:31]([O:40][CH3:41])=[CH:30][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:8]=[C:9]([O:10][CH3:11])[C:4]([O:3][CH2:1][CH3:2])=[C:5]([O:43][CH3:44])[CH:6]=4)=[N:13][CH:14]=3)[CH3:42])=[CH:28][N:27]=2)=[CH:34][C:33]=1[O:35][CH3:36])[CH3:39]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 22485531HCID 22485531, compound

Product 1

HCID 22485619HCID 22485619, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N,N′-bis[2-(4-ethoxy-3,5-dimethoxy-phenyl)-5-pyridyl]-N,N′-dimethylethylenediamine (133.0 mg, 0.220 mmol) in methanol (2.0 mL) was added a 1.0 M aqueous methanesulfonic acid solution (0.44 mL, 0.44 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-diethyl ether to afford the title compound as a yellow crystalline powder (melting point: 232.0-234.0° C. )(120.0 mg, yield: 54%).

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-diethyl ether

Sources & evidence

ORD record
ord-859c24099dbb4d24b718461369574362
Source dataset
uspto-grants-2005_05
Patent number
US06890940B2

Reaction notes

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