Methyl iodide → 7-Chloro-4-methyl-3-methylsulfanyl-4H-1,2,4-benzothiadiazine 1,1-dioxide

HRID 1066154Notes

Reaction equation

HRID 1066154 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]2[NH:6][C:7]([S:12][CH3:13])=[N:8][S:9](=[O:11])(=[O:10])[C:4]=2[CH:3]=1.[C:16](=O)([O-])[O-].[K+].[K+].CI>C(#N)C.CO>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]2[N:6]([CH3:16])[C:7]([S:12][CH3:13])=[N:8][S:9](=[O:11])(=[O:10])[C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 127001067-Chloro-3-(methylthio)-4H-benzo[e][1,2,4]thiadiazine 1,1-dioxide

Product 1

HCID 211978047-Chloro-4-methyl-3-methylsulfanyl-4H-1,2,4-benzothiadiazine 1,1-dioxide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 7-chloro-3-methylsulfanyl-4H-1,2,4-benzothiadiazine 1,1-dioxide (0.8 g) in acetonitrile (24 mL) and methanol (0.5 mL) was supplemented with potassium carbonate (0.96 g), then with methyl iodide (3 mL), and stirred at room temperature for 10 h. The solvent was removed by distillation under reduced pressure. The residue was suspended in water (40 mL) and the pH was adjusted to pH 2 with formic acid. The precipitate of the title compound was collected by filtration, washed with water and dried. The compound was used without further purification in the next step (yield: 0.53 g).

Workup

  1. customThe solvent was removed by distillation under reduced pressure
  2. filtrationThe precipitate of the title compound was collected by filtration
  3. washwashed with water
  4. customdried
  5. customThe compound was used without further purification in the next step (yield: 0.53 g)

Sources & evidence

ORD record
ord-11bd17b8349c44cca3c109fcea3c9034
Source dataset
uspto-grants-2001_06
Patent number
US06242443B1

Reaction notes

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