Methyl iodide → HCID 22397147, compound

HRID 411221Notes

Reaction equation

HRID 411221 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].IC.[CH3:9][C:10]1[CH:11]=[CH:12][C:13]2[NH:18][N:17]=[C:16]([C:19]([O:21][CH3:22])=[O:20])[S:15](=[O:24])(=[O:23])[C:14]=2[CH:25]=1.C(Cl)Cl>CN(C=O)C>[CH3:1][N:18]1[C:13]2[CH:12]=[CH:11][C:10]([CH3:9])=[CH:25][C:14]=2[S:15](=[O:23])(=[O:24])[C:16]([C:19]([O:21][CH3:22])=[O:20])=[N:17]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 22397196HCID 22397196, compound

Product 1

HCID 22397147HCID 22397147, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (2.25 g) and iodomethane (0.60 g) is added to a solution of methyl 6-methyl-1H-4,1,2-benzothiadiazine-3-carboxylate 4,4-dioxide (Preparation 39, 0.83 g) in DMF (20 mL). The mixture is stirred at room temperature for 5 hours and then added to CH2Cl2 (120 mL) and washed with water (4×100 mL). The organic layer is dried with Na2SO4, filtered and the solvent evaporated. The crude solid is recrystallized (1% CH2Cl2/MeOH) to obtain 0.74 g (85%) of the title compound as a yellow crystalline solid. Physical characteristics: MS (ESI+) m/z 269 (M+H).

Workup

  1. washwashed with water (4×100 mL)
  2. dry with materialThe organic layer is dried with Na2SO4
  3. filtrationfiltered
  4. customthe solvent evaporated
  5. customThe crude solid is recrystallized (1% CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-bcbb009531fb40e18f592b663aa20b74
Source dataset
uspto-grants-2003_05
Patent number
US06559145B2

Reaction notes

Loading…