Methanol → HCID 57837885, compound

HRID 731932Notes

Reaction equation

HRID 731932 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:12]NC(=O)C[C:8]=2[CH:14]=1)([O-:3])=[O:2].[H-].[Na+].[CH3:17]I.CO.[CH3:21][N:22]([CH:24]=[O:25])C>O>[CH3:21][N:22]1[C:8]2[CH:14]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=2[S:12][CH2:17][C:24]1=[O:25]

Participants

7

Reactant 5

HCID 887MethanolHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68706219HCID 68706219, compound

Product 1

HCID 57837885HCID 57837885, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In 11.5 ml of DMF was dissolved 500 mg of 6-nitro-2H-benzothiazin-3(4H)-one, and thereto was added 114 mg of sodium hydride of 55% purity under ice cooling, followed by 30 minutes of stirring at room temperature. To the reaction solution was added 444 μl of methyl iodide, and the whole was stirred at room temperature for 2 hours. To the reaction solution was added 2 ml of methanol under ice cooling, followed by 10 minutes of stirring at room temperature. Thereafter, water was added and the organic layer was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then the solvent was removed by evaporation. The obtained residue was purified by silica gel column chromatography (chloroform) to obtain 308 mg of 4-methyl-6-nitro-2H-1,4-benzothiazin-3(4H)-one.

Workup

  1. stirringthe whole was stirred at room temperature for 2 hours
  2. waitfollowed by 10 minutes
  3. stirringof stirring at room temperature
  4. extractionthe organic layer was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was removed by evaporation
  7. customThe obtained residue was purified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-57ea45fbc8a0490490a72c3673b73a75
Source dataset
uspto-grants-2009_09
Patent number
US07585878B2

Reaction notes

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