Water → HCID 15512313, compound

HRID 1490336Notes

Reaction equation

HRID 1490336 reaction equation
Cl[CH2:2][C:3]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=2)[N:4]=1.[C-:27]#[N:28].[K+].O>CS(C)=O>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=1)[N:4]=[C:3]2[CH2:2][C:27]#[N:28]

Participants

5

Reactant 3

HCID 962WaterHCID 9032Potassium CyanideHCID 15512312HCID 15512312, compound

Product 1

HCID 15512313HCID 15512313, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In 1000 ml of dimethyl sulfoxide was dissolved 187.0 g of 3-chloromethyl-5,6-dimethoxy-1-(3,4-dimethoxybenzyl)-1H-indazole, followed by stirring at room temperature. To the solution was added 134.0 g of potassium cyanide, having been ground to powder in a mortar, followed by stirring at 50° C. for 2 hours. The reaction mixture was cooled to room temperature, poured into 15000 ml of water, and stirred for 1 hour. A precipitated solid was collected, washed with three 1000 ml portions of water, dissolved in 5000 ml of chloroform, dried over sodium sulfate, filtered, and the solvent was evaporated. The residue was purified by silica gel column chromatography using 2 kg of silica gel and chloroform:ethanol=50:1 and then 2 kg of silica gel and ethyl acetate:hexane=3:1, to yield 111.0 g of a pale brown solid. This solid was used in the subsequent reaction without further purification.

Workup

  1. stirringby stirring at 50° C. for 2 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. stirringstirred for 1 hour
  4. customA precipitated solid was collected
  5. washwashed with three 1000 ml portions of water
  6. dissolutiondissolved in 5000 ml of chloroform
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customthe solvent was evaporated
  10. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7fae5b1f62374c5388fd9174fad36887
Source dataset
uspto-grants-1997_10
Patent number
US05681954

Reaction notes

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