Water → 4-(1-ethoxyimino-ethyl)-N-methyl-N-pyridin-4-ylmethyl-phenylsulfonamide

HRID 132545Notes

Reaction equation

HRID 132545 reaction equation
[CH2:1]([O:3][N:4]=[C:5]([C:7]1[CH:12]=[CH:11][C:10]([S:13]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)(=[O:15])=[O:14])=[CH:9][CH:8]=1)[CH3:6])[CH3:2].[H-].[Na+].I[CH3:27].O>CN(C)C=O>[CH2:1]([O:3][N:4]=[C:5]([C:7]1[CH:8]=[CH:9][C:10]([S:13]([N:16]([CH3:27])[CH2:17][C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)(=[O:15])=[O:14])=[CH:11][CH:12]=1)[CH3:6])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 727569504-(1-ethoxyiminoethyl)-N-pyridin-4-ylmethylphenylsulfonamide

Product 1

HCID 866097204-(1-ethoxyimino-ethyl)-N-methyl-N-pyridin-4-ylmethyl-phenylsulfonamideYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
22.5 °C

Procedure

0.4 g (1.2 mmol) of the compound from Example 2 was added to a slurry of 0.04 g (1.32 mmol) of NaH (95% pure) in 50 ml of dimethylformamide (DMF), and the mixture was then stirred at 20-25° C. for 10 min. A solution of 0.17 g (1.2 mmol) of iodomethane in 10 ml of DMF was then added dropwise, and the combined reaction solution was stirred at 20-25° C. for about 18 hours, poured into water and then extracted with MtBE. The the organic phases were washed with water and then dried. Removal of the solvent gave 0.3 g of the title compound as a viscous oil.

Workup

  1. customthe combined reaction solution
  2. stirringwas stirred at 20-25° C. for about 18 hours
  3. extractionextracted with MtBE
  4. washThe the organic phases were washed with water
  5. customdried
  6. customRemoval of the solvent

Sources & evidence

ORD record
ord-93e790a8df8e4c56adf51276c6f9451e
Source dataset
uspto-grants-2008_06
Patent number
US07388018B2

Reaction notes

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