Diethylcarbamoyl chloride → N,N-Diethyl-N'-[2-[6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]ethyl]urea

HRID 499498Notes

Reaction equation

HRID 499498 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+].[CH2:34]([N:36]([CH2:40][CH3:41])[C:37](Cl)=[O:38])[CH3:35]>C(#N)C>[CH2:34]([N:36]([CH2:40][CH3:41])[C:37]([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:38])[CH3:35]

Participants

5

Reactant 3

HCID 6916Diethylcarbamoyl chlorideHCID 11430Potassium CarbonateHCID 684539582-[6-(2-Aminoethyl)-2-pyridyl]-4h-1,3-benzothiazine-4-one trifluoroacetic acid salt

Product 1

HCID 59750111N,N-Diethyl-N'-[2-[6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]ethyl]ureaYield 31.4%

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 (0.40 g, 1.0 mmol), potassium carbonate (0.41 g, 3.0 mmol) and acetonitrile (20 ml) was stirred at room temperature for 20 minutes. Successively N,N-diethylcarbamoyl chloride (0.54 g, 4.0 mmol) was added to the mixture, and the mixture was stirred at room temperature for 4 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 (30:1, v/v) were collected, concentrated and recrystallized from ethanol-hexane to give the titled compound (0.12 g, 31%) as white crystals.

Workup

  1. stirringthe mixture was stirred at room temperature for 4 hrs
  2. filtrationThe precipitates were filtered
  3. concentrationthe filtrate was concentrated
  4. washThe fractions eluted with chloroform-ethanol (30:1
  5. customv/v) were collected
  6. concentrationconcentrated
  7. customrecrystallized from ethanol-hexane

Sources & evidence

ORD record
ord-f2150826a531408f976b39551b56a768
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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