Methyl iodide → HCID 21849830, compound

HRID 617776Notes

Reaction equation

HRID 617776 reaction equation
[CH3:1][N:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([OH:12])[C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[S:3]1.[C:17](=O)([O-])[O-].[K+].[K+].IC>CC(C)=O>[CH3:1][N:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([O:12][CH3:17])[C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[S:3]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 54683830HCID 54683830, compound

Product 1

HCID 21849830HCID 21849830, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

This compound was prepared according to Zinnes et. al., J. Med. Chem., 1973, 16, 44-48. Thus, a solution of methyl 2-methyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate (500 mg, 1.86 mmol) (Lombardino, et. al., J. Med. Chem., 1971, 14, 1171-1177, incorporated by reference herein in its entirety) in acetone (10 ml) was treated with anhydrous potassium carbonate (2.6 g, 18.6 mmol) and iodomethane (1.32 g, 9.29 mmol) and refluxed for 40 hours. The mixture was filtered and concentrated and the residue was partitioned between ethyl acetate and water. The organic phase was washed with saturated aqueous sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, filtered and concentrated to afford 285 mg (54%) of the title compound as a yellow viscous oil, used subsequently without need for further purification; NMR (CDCl3) δ 3.03 (s, 3H), 3.83 (s, 3H), 3.91 (s, 3H), 7.67-7.72 (m, 2H), 7.81-7.88 (m, 2H); MS: 284 m/z (M+H)+.

Workup

  1. customThis compound was prepared
  2. temperaturerefluxed for 40 hours
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated
  5. customthe residue was partitioned between ethyl acetate and water
  6. washThe organic phase was washed with saturated aqueous sodium bicarbonate and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-cbe798e3ac414f40a6c00edfaa3327fd
Source dataset
uspto-grants-1999_09
Patent number
US05952328

Reaction notes

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