Methyl iodide → HCID 86600614, compound

HRID 859852Notes

Reaction equation

HRID 859852 reaction equation
[H-].[Na+].[Cl:3][C:4]1[N:9]=[CH:8][C:7]([CH2:10][NH:11][C:12](=[O:27])[C:13](=[N:15][NH:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)[CH3:14])=[CH:6][CH:5]=1.CI.[C:30](OCC)(=O)C>CN(C)C=O>[Cl:3][C:4]1[N:9]=[CH:8][C:7]([CH2:10][NH:11][C:12](=[O:27])[C:13](=[N:15][N:16]([CH3:30])[C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:24])([F:25])[F:26])=[CH:19][CH:18]=2)[CH3:14])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 73062855HCID 73062855, compound

Product 1

HCID 86600614HCID 86600614, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

60% sodium hydride (0.12 g, 3.0 mmol) was added to a solution of N-(6-chloro-3-pyridylmethyl)-2-(4-trifluoromethylphenyl hydrazono) propionic acid amide (Compound No. 63) (1.0 g, 2.7 mmol) in N,N-dimethylformamide (5 ml) and stirred for 10 minutes. Methyl iodide (0.40 g, 2.8 mmol) was gradually added thereto, and stirred at room temperature for 2 hours. To the reaction mixture, ice water and ethyl acetate were added, and subjected to extraction. The organic phase was washed with a saturated brine, then dried on anhydrous sodium sulfate and concentrated. The resulting residue was purified with a silica gel chromatography to obtain N-(6-chloro-3-pyridylmethyl)-2-[N-methyl-N-(4-trifluoromethylphenyl) hydrazono]propionic acid amide (Compound No. 110) (0.80 g, 2.1 mmol, 77%).

Workup

  1. stirringstirred at room temperature for 2 hours
  2. extractionsubjected to extraction
  3. washThe organic phase was washed with a saturated brine
  4. dry with materialdried on anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe resulting residue was purified with a silica gel chromatography

Sources & evidence

ORD record
ord-1d793b306aaf423aa3f54fc8b1013c9a
Source dataset
uspto-grants-2006_12
Patent number
US07153815B2

Reaction notes

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