Methyl iodide → HCID 13472716, compound

HRID 2412329Notes

Reaction equation

HRID 2412329 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[C:19]3[C:15](=[N:16][O:17][N:18]=3)[CH:14]=[CH:13][CH:12]=2)[C:9]([C:20]([O:22][CH:23]([CH3:25])[CH3:24])=[O:21])=[C:8]([CH3:26])[NH:7][N:6]=1)=[O:4].[OH-].[K+].[CH3:29]I>CS(C)=O>[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[C:19]3[C:15](=[N:16][O:17][N:18]=3)[CH:14]=[CH:13][CH:12]=2)[C:9]([C:20]([O:22][CH:23]([CH3:24])[CH3:25])=[O:21])=[C:8]([CH3:26])[N:7]([CH3:29])[N:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 13472713HCID 13472713, compound

Product 1

HCID 13472716HCID 13472716, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To the solution of 3.2 g of 4-(2,1,3-benzoxadiazol-4-yl)-1,4-dihydro-5-isopropoxycarbonyl-6-methyl-3-pyridazine carboxylic acid methylester (I R4 =H, R3 =CH3, R1 =CH3, R2 =isopropyl) in 60 ml of dimethyl sulphoxide are added 2.0 g of powdered potassium hydroxide, and then 1.1 ml of methyl iodide are dropwise added. The mixture is stirred for 45 minutes at room temperature, and is then poured into 120 ml of ice water and extracted with methylene chloride. The product obtained after drying the methylene chloride solution over magnesium sulphate and evaporating under vacuum is purified by chromatography on silica gel. After elution with methylene chloride - ether mixtures and subsequent crystallization from ether - petroleum ether, the pure substance is obtained with a m.p. of 107° .

Workup

  1. extractionextracted with methylene chloride
  2. customThe product obtained
  3. dry with materialafter drying the methylene chloride solution over magnesium sulphate
  4. customevaporating under vacuum
  5. customis purified by chromatography on silica gel
  6. washAfter elution
  7. customwith methylene chloride - ether mixtures and subsequent crystallization from ether - petroleum ether
  8. customthe pure substance is obtained with a m.p. of 107°

Sources & evidence

ORD record
ord-eeea959c72fb484db6576f12907fae31
Source dataset
uspto-grants-1985_01
Patent number
US04491581

Reaction notes

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