Benzoyl chloride → N-[2-[6-(4-Oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]ethyl]benzamide

HRID 499493Notes

Reaction equation

HRID 499493 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:28](Cl)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C(=O)C.O>[O:23]=[C:21]1[C:20]2[CH:24]=[CH:25][CH:26]=[CH:27][C:19]=2[S:18][C:17]([C:15]2[N:16]=[C:11]([CH2:10][CH2:9][NH:8][C:28](=[O:35])[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:12]=[CH:13][CH:14]=2)=[N:22]1

Participants

7

Reactant 4

HCID 7412Benzoyl chlorideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 684539582-[6-(2-Aminoethyl)-2-pyridyl]-4h-1,3-benzothiazine-4-one trifluoroacetic acid salt

Product 1

HCID 59750436N-[2-[6-(4-Oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]ethyl]benzamideYield 26%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
60 °C

Procedure

2-[6-(2-Aminoethyl)-2-pyridyl]-4H-1,3-benzothiazine-4-one trifluoroacetic acid salt (0.53 g, 1.3 mmol) was dissolved in N,N-dimethylacetamide (10 ml), and benzoyl chloride (0.38 g, 2.7 mmol) and potassium carbonate (0.18 g, 1.3 mmol) were added thereto. The reaction mixture was stirred at 60° C. for 4 hrs, combined with ethyl acetate and water. The organic layer was successively washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with methanol-ethyl acetate (1:20, v/v) were collected, concentrated and recrystallized from hexane-ethanol to give the titled compound (0.13 g, 26%) as white crystals.

Workup

  1. washThe organic layer was successively washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated
  4. washThe fractions eluted with methanol-ethyl acetate (1:20
  5. customv/v) were collected
  6. concentrationconcentrated
  7. customrecrystallized from hexane-ethanol

Sources & evidence

ORD record
ord-1c31a2c8bb7c448ebf0ae5cdcfc343b8
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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