Dimethylacetamide → HCID 22939299, compound

HRID 499358Notes

Reaction equation

HRID 499358 reaction equation
[CH3:1][NH:2][C:3]1[N:8]=[C:7]([C:9]2[S:10][C:11]3[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=3[C:13](=[O:15])[N:14]=2)[CH:6]=[CH:5][CH:4]=1.[C:20](Cl)(=[O:23])[CH2:21][CH3:22].CN(C)C(=O)C>O>[CH3:1][N:2]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([C:9]2[S:10][C:11]3[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=3[C:13](=[O:15])[N:14]=2)[N:8]=1)[C:20](=[O:23])[CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 31374DimethylacetamideHCID 62324Propionyl chlorideHCID 22939297HCID 22939297, compound

Product 1

HCID 22939299HCID 22939299, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-(6-methylamino-2-pyridyl)-4H-1,3-benzothiazine-4-one (0.25 g, 0.92 mmol), propionyl chloride (0.29 g, 3.1 mmol) and N,N-dimethylacetamide (10 ml) was stirred at 80° C. for 2 hrs. After cooling, the reaction mixture was poured into water and extracted with ethyl acetate. The extract was successively washed with saturated aqueous sodium hydrogen carbonate solution and brine and dried. The solvent was evaporated. The residue was recrystallized from tetrahydrofuran-hexane to give the titled compound (0.15 g, 49%).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe extract was successively washed with saturated aqueous sodium hydrogen carbonate solution and brine
  4. customdried
  5. customThe solvent was evaporated
  6. customThe residue was recrystallized from tetrahydrofuran-hexane

Sources & evidence

ORD record
ord-a2299fb15a624fbf965a87385b717bd5
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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