Water → HCID 15512313, compound

HRID 356593Notes

Reaction equation

HRID 356593 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].[Na+].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 8929Sodium CyanideHCID 15512312HCID 15512312, compound

Product 1

HCID 15512313HCID 15512313, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3-Chloromethyl-5,6-dimethoxy-1-(3,4-dimethoxybenzyl)-1H-indazole (187.0 g) was dissolved in dimethyl sulfoxide (1000 ml) and a solution was stirred at room temperature. Then sodium cyanide (134.0 g) which had been ground in a mortar was added thereto. The reaction mixture was stirred at 50° C. for 2 hours. The reaction mixture was returned to room temperature, poured into water (15000 ml) and stirred for 1 hour. The solid thus precipitated was collected by filtration, washed with water (1000 ml×3), dissolved in chloroform (5000 ml), dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue thus obtained was purified by using silica gel columns (chloroform/ethanol 50/1, silica gel 2 kg, followed by silica gel 2 kg, ethyl acetate/hexane=3:1) to give 111.0 g of a pale brown solid product. This solid product was used in the subsequent reaction without purification.

Workup

  1. additionwas added
  2. stirringThe reaction mixture was stirred at 50° C. for 2 hours
  3. customwas returned to room temperature
  4. stirringstirred for 1 hour
  5. customThe solid thus precipitated
  6. filtrationwas collected by filtration
  7. washwashed with water (1000 ml×3)
  8. dissolutiondissolved in chloroform (5000 ml)
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. customevaporated under reduced pressure
  12. customThe residue thus obtained
  13. customwas purified

Sources & evidence

ORD record
ord-30e2f0c640da4d5989d1dba288b21d87
Source dataset
uspto-grants-1998_11
Patent number
US05837706

Reaction notes

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