Water → 5,6-Dimethoxy-1-(1-trityl-4-imidazolyl)methyl-1H-indazole-3-acetonitrile

HRID 1490342Notes

Reaction equation

HRID 1490342 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[N:18]=[CH:19][N:20]([C:22]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:21]=2)[N:4]=1.[C-:41]#[N:42].[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[N:18]=[CH:19][N:20]([C:22]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:21]=1)[N:4]=[C:3]2[CH2:2][C:41]#[N:42]

Participants

5

Reactant 3

HCID 962WaterHCID 9032Potassium CyanideHCID 154286393-Chloromethyl-5,6-dimethoxy-1-(1-trityl-4-imidazolyl)methyl-1H-indazole

Product 1

HCID 154286405,6-Dimethoxy-1-(1-trityl-4-imidazolyl)methyl-1H-indazole-3-acetonitrileYield 67%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In 1200 ml of dimethyl sulfoxide was suspended 165.0 g of 3-chloromethyl-5,6-dimethoxy-1-(1-trityl-4-imidazolyl)methyl-1H-indazole, followed by stirring at room temperature. To the suspension was added 43.6 g of potassium cyanide, having been ground to powder in a mortar, and the mixture was stirred at 70° C. for 1 hour. The reaction mixture was cooled to room temperature and poured into 15000 ml of water with vigorous stirring, followed by stirring for 1 hour. A precipitated solid was collected, washed with three 1000 ml portions of water, and dissolved in 5000 ml of chloroform. The solution was dried over sodium sulfate, filtered, and the solvent was evaporated. Silica gel column chromatography (ethyl acetate) of the residue yielded 108.7 g of a pale brown solid, which was used in the next reaction as such.

Workup

  1. stirringthe mixture was stirred at 70° C. for 1 hour
  2. temperatureThe reaction mixture was cooled to room temperature
  3. stirringby stirring 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 materialThe solution was dried over sodium sulfate
  8. filtrationfiltered
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-c90bc7a73b244b1795af8d84fc6215b2
Source dataset
uspto-grants-1997_10
Patent number
US05681954

Reaction notes

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