Dimethylcarbamoyl Chloride → N,N-Dimethyl-N'-[2-[6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]ethyl]urea

HRID 499497Notes

Reaction equation

HRID 499497 reaction equation
FC(F)(F)C(O)=O.[NH2:8][CH2:9][CH2:10][C:11]1[N:16]=[C:15]([C:17]2[S:18][C:19]3[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=3[C:21](=[O:23])[N:22]=2)[CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:34][N:35]([CH3:39])[C:36](Cl)=[O:37]>C(#N)C>[CH3:34][N:35]([CH3:39])[C:36]([NH:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]([C:17]2[S:18][C:19]3[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=3[C:21](=[O:23])[N:22]=2)[N:16]=1)=[O:37]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 11430Potassium CarbonateHCID 684539582-[6-(2-Aminoethyl)-2-pyridyl]-4h-1,3-benzothiazine-4-one trifluoroacetic acid salt

Product 1

HCID 59750465N,N-Dimethyl-N'-[2-[6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]ethyl]ureaYield 79.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-[6-(2-aminoethyl)-2-pyridyl]-4H-1,3-benzothiazine-4-one trifluoroacetic acid salt (0.45 g, 1.1 mmol), potassium carbonate (0.46 g, 3.3 mmol) and acetonitrile (20 ml) 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 3 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 (20:1, v/v) were collected, concentrated and recrystallized from chloroform-hexane to give the titled compound (0.31 g, 77%) as white crystals.

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hrs
  2. filtrationThe precipitates were filtered
  3. concentrationthe filtrate was concentrated
  4. washThe fractions eluted with chloroform-ethanol (20:1
  5. customv/v) were collected
  6. concentrationconcentrated
  7. customrecrystallized from chloroform-hexane

Sources & evidence

ORD record
ord-89b935f4eec94e4c9070fd9cec6b22a2
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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