4-(Chloromethyl)-1-trityl-1H-imidazole → HCID 15428637, compound

HRID 1490340Notes

Reaction equation

HRID 1490340 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[NH:8][N:7]=[C:6]2[C:14]([O:16][CH2:17][CH3:18])=[O:15].C[O-].[Li+].Cl[CH2:23][C:24]1[N:25]=[CH:26][N:27]([C:29]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:28]=1>CS(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]([CH2:23][C:24]1[N:25]=[CH:26][N:27]([C:29]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[CH:28]=1)[N:7]=[C:6]2[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

5

Reactant 3

HCID 27631764-(Chloromethyl)-1-trityl-1H-imidazole2×HCID 4177230Lithium methanolate2×HCID 15428636Ethyl 5,6-dimethoxy-1H-indazole-3-carboxylate

Product 1

HCID 15428637HCID 15428637, compoundYield 38.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

In 5000 ml of dimethyl sulfoxide was suspended 250.2 g of ethyl 5,6-dimethoxyindazole-3-carboxylate, and 40.2 g of lithium methoxide was added to the suspension, followed by stirring at room temperature for 1 hour. A solution of 447.8 g of 4-chloromethyl-1-tritylimidazole in 2000 ml of dimethyl sulfoxide was added dropwise thereto at room temperature over 10 minutes. After stirring at room temperature for 2 hours, 4.2 g of lithium methoxide and 44.8 g of 4-chloromethyl-1-tritylimidazole were further added thereto, followed by stirring at room temperature for 1 hour. The reaction mixture was poured into 30000 ml of ice-water while stirring. A precipitated crystal was collected, washed with three 2000 ml portions of water, and dried. The solid was dissolved in 10000 ml of chloroform, and the solution was dried over sodium sulfate, filtered, and the solvent was evaporated. The residue was purified by silica gel column chromatography (chloroform:ethanol=50:1) and recrystallized from chloroform/isopropyl alcohol to yield 222.0 g of the title compound as a colorless prism crystal.

Workup

  1. additionwas added to the suspension
  2. waitat room temperature over 10 minutes
  3. stirringAfter stirring at room temperature for 2 hours
  4. stirringby stirring at room temperature for 1 hour
  5. stirringwhile stirring
  6. customA precipitated crystal was collected
  7. washwashed with three 2000 ml portions of water
  8. customdried
  9. dissolutionThe solid was dissolved in 10000 ml of chloroform
  10. dry with materialthe solution was dried over sodium sulfate
  11. filtrationfiltered
  12. customthe solvent was evaporated
  13. customThe residue was purified by silica gel column chromatography (chloroform:ethanol=50:1)
  14. customrecrystallized from chloroform/isopropyl alcohol

Sources & evidence

ORD record
ord-14ca3e482f4240c5845efebf62836697
Source dataset
uspto-grants-1997_10
Patent number
US05681954

Reaction notes

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