Dimethylcarbamoyl Chloride → N,N-Dimethyl-N'-[[6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]methyl]urea
Reaction equation
FC(F)(F)C(O)=O.[NH2:8][CH2:9][C:10]1[N:15]=[C:14]([C:16]2[S:17][C:18]3[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=3[C:20](=[O:22])[N:21]=2)[CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:33][N:34]([CH3:38])[C:35](Cl)=[O:36]>>[CH3:33][N:34]([CH3:38])[C:35]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]([C:16]2[S:17][C:18]3[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=3[C:20](=[O:22])[N:21]=2)[N:15]=1)=[O:36]Participants
4
Procedure
A mixture of 2-[6-(aminomethyl)-2-pyridyl]-4H-1,3-benzothiazine-4-one trifluoroacetic acid salt (0.40 g, 1.0 mmol) and potassium carbonate (0.43 g, 3.1 mmol) was stirred at room temperature for 20 minutes. Successively, N,N-dimethylcarbamoyl chloride (0.47 g, 4.3 mmol) was added to the mixture, and the mixture was stirred at room temperature for 5 hrs. The precipitates were filtered, and the filtrate was concentrated. The residue was subjected to a silica gel column chromatography. The fractions eluted with chloroform-ethanol (40:1, v/v) were collected, concentrated and recrystallized from chloroform-hexane to give the titled compound (0.24 g, 68%) as white crystals.
Workup
- stirringthe mixture was stirred at room temperature for 5 hrs
- filtrationThe precipitates were filtered
- concentrationthe filtrate was concentrated
- washThe fractions eluted with chloroform-ethanol (40:1
- customv/v) were collected
- concentrationconcentrated
- customrecrystallized from chloroform-hexane
Sources & evidence
- ORD record
- ord-518092d810f9434cb2f098f3909fe669
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07399759B2
Reaction notes
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