Water → HCID 19074438, compound

HRID 964944Notes

Reaction equation

HRID 964944 reaction equation
[S:1]1(=[O:13])(=[O:12])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH2:4][C:3](=[O:11])[NH:2]1.Cl[CH:15]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.[C:30](=[O:33])([O-:32])[O-].[K+].[K+].O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:3]([OH:11])(=[O:21])/[CH:4]=[CH:5]/[C:30]([OH:32])=[O:33].[O:21]1[CH2:22][CH2:23][N:18]([CH2:17][CH2:16][CH:15]([N:2]2[C:3](=[O:11])[CH2:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[S:1]2(=[O:12])=[O:13])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:19][CH2:20]1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1179723-Hydroxy-1lambda~6~,2-benzothiazine-1,1(4H)-dioneHCID 16767631HCID 16767631, compound

Product 1

HCID 19074438HCID 19074438, compoundYield 53.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In toluene (7 mL) were suspended 2H-1,2-benzothiazin-3(4H)-one 1,1-dioxide (250 mg, 1.3 mmol.), 1-chloro-3-morpholino-1-phenylpropane (340 mg, 1.4 mmol.), potassium carbonate (250 mg, 1.8 mmol.) and a catalytic amount of cupper powder. The suspension was heated for 12 hours under refluxing. The reaction liquid was cooled, and the insolubles were filtered off. The solvent was distilled off to leave a residue. To the residue were added water and ethyl acetate, and the organic layer was taken out. The organic solution was washed with water and an aqueous saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the resulting residue was treated by silica gel column chromatogrpahy (ethyl acetate) to give the free base of the desired compound (180 mg) as an oil. The free base was treated in the conventional manner to convert into the desired fumarate.

Workup

  1. temperatureThe suspension was heated for 12 hours
  2. temperatureunder refluxing
  3. customThe reaction liquid
  4. temperaturewas cooled
  5. filtrationthe insolubles were filtered off
  6. distillationThe solvent was distilled off
  7. customto leave a residue
  8. washThe organic solution was washed with water
  9. dry with materialan aqueous saturated sodium chloride solution, and dried over anhydrous sodium sulfate
  10. distillationThe solvent was distilled off
  11. additionthe resulting residue was treated by silica gel column chromatogrpahy (ethyl acetate)

Sources & evidence

ORD record
ord-0d30936c5c4b4103b4ece3eb66b324f1
Source dataset
uspto-grants-1998_06
Patent number
US05773437

Reaction notes

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