Dimethylacetamide → HCID 22939583, compound

HRID 499355Notes

Reaction equation

HRID 499355 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.[S:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[C:25](Cl)=[O:26].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:25]([C:21]1[S:20][CH:24]=[CH:23][CH:22]=1)=[O:26]

Participants

5

Reactant 3

HCID 31374DimethylacetamideHCID 789282-Thiophenecarbonyl chlorideHCID 22939297HCID 22939297, compound

Product 1

HCID 22939583HCID 22939583, compoundYield 83%

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 (0.20 g, 0.74 mmol), 2-thiophenecarbonyl chloride (0.28 g, 1.9 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 washed successively 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 (0.23 g, 83%).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed successively 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-558253fa1cfd42228a9e63e48536a3c4
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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