Methyl iodide → HCID 178480778, compound

HRID 437123Notes

Reaction equation

HRID 437123 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]=[C:7]([N:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[NH:8][S:9](=[O:11])(=[O:10])[C:4]=2[CH:3]=1.CI.[C:22](=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]=[C:7]([N:12]3[CH2:17][CH2:16][N:15]([CH3:22])[CH2:14][CH2:13]3)[NH:8][S:9](=[O:10])(=[O:11])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 178527169HCID 178527169, compound

Product 1

HCID 178480778HCID 178480778, compoundYield 38.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.0 g of 7-chloro-3-(1-piperazinyl)-2H-1,2,4-benzothiadiazine 1,1-dioxide in 15 ml of dimethylformamide is added dropwise at 0° C. 0.56 g of 93% methyl iodide, in the presence of 0.7 g of anhydrous sodium carbonate. The mixture is stirred for 2 hours, while the temperature is kept at 0° C. After removal of dimethylformamide by distillation under reduced pressure, the resulting residue is triturated with 10 ml of water to precipitate the crystals. The collected precipitate is recrystallized from a mixture of dimethylformamide and water to give 0.4 g of the desired product, m.p. above 300° C.

Workup

  1. customis kept at 0° C
  2. customAfter removal of dimethylformamide
  3. distillationby distillation under reduced pressure
  4. customthe resulting residue is triturated with 10 ml of water
  5. customto precipitate the crystals
  6. customThe collected precipitate is recrystallized from a mixture of dimethylformamide and water

Sources & evidence

ORD record
ord-03d797172a8644649b55d87d9df36ff6
Source dataset
uspto-grants-1977_06
Patent number
US04029780

Reaction notes

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