Water → HCID 19074408, compound

HRID 964945Notes

Reaction equation

HRID 964945 reaction equation
[S:1]1(=[O:13])(=[O:12])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4](=[O:11])[NH:3][CH2:2]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>C(C(C)=O)C.C(OCC)(=O)C>[C:4]([OH:11])(=[O:21])/[CH:5]=[CH:10]/[C:30]([OH:32])=[O:33].[O:21]1[CH2:22][CH2:23][N:18]([CH2:17][CH2:16][CH:15]([N:3]2[C:4](=[O:11])[C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[S:1](=[O:12])(=[O:13])[CH2:2]2)[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 343244779726-08-2HCID 16767631HCID 16767631, compound

Product 1

HCID 19074408HCID 19074408, compoundYield 52.3%

Reagents, catalysts & solvents 2

HCID 6569Methyl Ethyl KetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In methyl ethyl ketone (5 mL) were suspended 2H-1,3-benzothiazin-4(3H)-one 1,1-dioxide (100 mg, 0.518 mmol.), 1-chloro-3-morpholino-1-phenylpropane (130 mg, 0.54 mmol.), and potassium carbonate (180 mg, 1.3 mmol.). The suspension was heated overnight under refluxing. The reaction liquid was cooled, and the insolubles were filtered off. The solvent was distilled off to give 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 residue was treated by silica gel column chromatography (chloroform/methanol=50/1) to give the free base of the desired compound (70 mg, yield 35%) as an oil.

Workup

  1. temperatureThe suspension was heated overnight
  2. temperatureunder refluxing
  3. customThe reaction liquid
  4. temperaturewas cooled
  5. filtrationthe insolubles were filtered off
  6. distillationThe solvent was distilled off
  7. customto give 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 residue was treated by silica gel column chromatography (chloroform/methanol=50/1)

Sources & evidence

ORD record
ord-0b3e7e26504a405bb0b1e32ad78c4969
Source dataset
uspto-grants-1998_06
Patent number
US05773437

Reaction notes

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