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

HRID 2258469Notes

Reaction equation

HRID 2258469 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

3-Chloromethyl-5,6-dimethoxy-1(1-trityl-4-imidazolyl)methyl-1H-indazole (165.0 g) was suspended in dimethyl sulfoxide (1200 ml) and the solution was stirred at room temperature. Then potassium cyanide (43.6 g), which had been ground in a mortar, was added thereto. After stirring at 70° C. for 1 hour, the reaction mixture became homogeneous and transparent. The reaction mixture was returned to room temperature and poured into water (15000 ml) while vigorously stirring. The stirring was continued 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 a silica gel column (ethyl acetate) to give 108.7 g of a pale brown solid. This solid product was used in the subsequent reaction without purification.

Workup

  1. additionwas added
  2. stirringAfter stirring at 70° C. for 1 hour
  3. customwas returned to room temperature
  4. stirringwhile vigorously stirring
  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-d1090638468e4e1bb832d35f99fd4552
Source dataset
uspto-grants-1997_08
Patent number
US05661150

Reaction notes

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