Dimethylformamide → 3-(3-Oxo-3-phenylpropyl)-1H-2,3-benzothiazin-4(3H)-one 2,2-Dioxide

HRID 964948

Reaction equation

HRID 964948 reaction equation
[CH2:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4](=[O:11])[NH:3][S:2]1(=[O:13])=[O:12].[OH-].[K+].Cl[CH2:17][CH2:18][C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:20].CN(C)C=O>CO>[O:20]=[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:18][CH2:17][N:3]1[C:4](=[O:11])[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[CH2:1][S:2]1(=[O:12])=[O:13]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 14797Potassium HydroxideHCID 702953-ChloropropiophenoneHCID 890421H-2,3-Benzothiazin-4(3H)-one 2,2-dioxide

Product 1

HCID 190744233-(3-Oxo-3-phenylpropyl)-1H-2,3-benzothiazin-4(3H)-one 2,2-DioxideYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1H-2,3-Benzothiazin-4(3H)-one 2,2-dioxide (1 g, 5.08 mmol.) was added to a solution of powdery potassium hydroxide (334 mg, 5.08 mmol.) in methanol (4 mL). The mixture was then stirred at room temperature for 15 min. The solution was placed under reduced pressure to distill the solvent off to dryness. To the dried product were added 3-chloropropiophenone (856 mg, 5.08 mmol.) and dimethylformamide (8 mL). The mixture was heated to 120° C. for 6 hours under stirring. The reaction liquid was placed under reduced pressure to distill the solvent off. To the resulting residue was added water, and it was extracted with ethyl acetate. The extract solution was washed with an aqueous saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The dried extract solution was placed under reduced pressure to distill the solvent off. The resulting oil was treated by silica gel column chromatography (chloroform) to give the desired compound (1.13 g, yield 68%) as a white solid.

Workup

  1. distillationto distill the solvent off to dryness
  2. temperatureThe mixture was heated to 120° C. for 6 hours
  3. stirringunder stirring
  4. customThe reaction liquid
  5. distillationto distill the solvent off
  6. additionTo the resulting residue was added water, and it
  7. extractionwas extracted with ethyl acetate
  8. washThe extract solution was washed with an aqueous saturated sodium chloride solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. extractionThe dried extract solution
  11. distillationto distill the solvent off
  12. additionThe resulting oil was treated by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-4ded7243862b45d28d9890b39ac01a35
Source dataset
uspto-grants-1998_06
Patent number
US05773437

Linked notes

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