Sodium Cyanide → HCID 68284963, compound

HRID 571607Notes

Reaction equation

HRID 571607 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12]1[C:13](=[O:29])[N:14]([CH3:28])[N:15]=[C:16]([CH2:26]Br)[C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:2].[C-:30]#[N:31].[Na+]>CS(C)=O.O>[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12]1[C:13](=[O:29])[N:14]([CH3:28])[N:15]=[C:16]([CH2:26][C:30]#[N:31])[C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:2]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 68284889HCID 68284889, compound

Product 1

HCID 68284963HCID 68284963, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 4-(2,6-diethyl-4-methylphenyl)-6-bromomethyl-5-benzyloxy-2-methyl-3(2H)-pyridazinone (675 mg, 1.48 mmol) in DMSO (4 ml) was added sodium cyanide (80 mg, 1.63 mmol), and stirred at room temperature for 30 minutes. The reaction solution was diluted with water, and extracted with ethyl acetate 2 times. The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give 405 mg of Compound (I-30) (yield: 66%) as solid.

Workup

  1. extractionextracted with ethyl acetate 2 times
  2. washThe combined organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-5f486ab2269344b4b9fe9913ce5fff28
Source dataset
uspto-grants-2015_05
Patent number
US09029295B2

Reaction notes

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