Methanesulfonic Acid → 1,4-Bis[5-(3,4,5-trimethoxyphenyl)-2-pyridyl]hexahydro-1,4-diazepine dimethanesulfonate
Reaction equation
[O:1]([C:4]1[CH:5]=[C:6]([C:16]2[CH:17]=[CH:18][C:19]([N:22]3[CH2:28][CH2:27][CH2:26][N:25]([C:29]4[CH:34]=[CH:33][C:32]([C:35]5[CH:40]=[C:39]([O:41][CH2:42]C)[C:38]([O:44][CH2:45]C)=[C:37]([O:47][CH2:48]C)[CH:36]=5)=[CH:31][N:30]=4)[CH2:24][CH2:23]3)=[N:20][CH:21]=2)[CH:7]=[C:8]([O:13][CH2:14]C)[C:9]=1[O:10][CH2:11]C)[CH2:2]C.[CH3:50][S:51]([OH:54])(=[O:53])=[O:52]>C(O)C.C(Cl)(Cl)Cl>[CH3:50][S:51]([OH:54])(=[O:53])=[O:52].[CH3:50][S:51]([OH:54])(=[O:53])=[O:52].[CH3:42][O:41][C:39]1[CH:40]=[C:35]([C:32]2[CH:33]=[CH:34][C:29]([N:25]3[CH2:26][CH2:27][CH2:28][N:22]([C:19]4[CH:18]=[CH:17][C:16]([C:6]5[CH:5]=[C:4]([O:1][CH3:2])[C:9]([O:10][CH3:11])=[C:8]([O:13][CH3:14])[CH:7]=5)=[CH:21][N:20]=4)[CH2:23][CH2:24]3)=[N:30][CH:31]=2)[CH:36]=[C:37]([O:47][CH3:48])[C:38]=1[O:44][CH3:45]Participants
4
Procedure
To a solution of 1,4-bis[5-(3,4,5-triethoxylphenyl)-2-pyridyl]hexahydro-1,4-diazepine (72.4 g, 0.120 mol) in ethanol-chloroform (1:3, 600 mL) was added methanesulfonic acid (24.9 g, 0.258 mol), and the reaction mixture was concentrated under reduced pressure. The residue was recrystallized from methanol-diethyl ether to yield the title compound as a slightly yellow crystalline powder (melting point: 204.0–206.0° C.) (88.2 g, yield: 92%).
Workup
- concentrationthe reaction mixture was concentrated under reduced pressure
- customThe residue was recrystallized from methanol-diethyl ether
Sources & evidence
- ORD record
- ord-23069f42d58b45d7836c1c1920995f68
- Source dataset
- uspto-grants-2007_03
- Patent number
- US07196101B2
Reaction notes
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