Water → HCID 583630, compound

HRID 722943Notes

Reaction equation

HRID 722943 reaction equation
[H-].[Na+].[NH:3]1[C:7]2C=[CH:9][CH:10]=[CH:11][C:6]=2N[S:4]1(=[O:13])=[O:12].[CH3:14]I.O.C[N:18]([CH3:21])[CH:19]=O>>[CH3:21][N:18]1[C:19]2[CH:9]=[CH:10][CH:11]=[CH:6][C:7]=2[N:3]([CH3:14])[S:4]1(=[O:13])=[O:12]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 153721H,3H-2,1,3-Benzothiadiazole 2,2-dioxideHCID 24758Sodium hydride

Product 1

HCID 583630HCID 583630, compound

Procedure

Sodium hydride (5 g) was added to a solution of 1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide (10 g) obtained in Reference Example 126 in dimethylformamide (100 ml), the mixture was stirred at room temperature for 1 hour, methyl iodide was added, and the mixture was stirred at room temperature for 18 hours. Water (200 g) was poured into the reaction mixture, extracted with ethyl acetate, and washed with brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give a reddish brown solid (9.9 g). Further recrystallization from water-ethyl acetate afforded the title compound as colorless crystals (9.0 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 18 hours
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c008f8edafc14459842f4af700eaaefc
Source dataset
uspto-grants-2006_11
Patent number
US07138533B2

Reaction notes

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