Thionyl Chloride → 3-Chloromethyl-5,6-dimethoxy-1-(1-trityl-4-imidazolyl)methyl-1H-indazole

HRID 2258468Notes

Reaction equation

HRID 2258468 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])[N:8]([CH2:14][C:15]1[N:16]=[CH:17][N:18]([C:20]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:19]=1)[N:7]=[C:6]2[CH2:39]O.S(Cl)([Cl:43])=O.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:43][CH2:39][C:6]1[C:5]2[C:9](=[CH:10][C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:8]([CH2:14][C:15]2[N:16]=[CH:17][N:18]([C:20]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:19]=2)[N:7]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 154286385,6-dimethoxy-1-(1-trityl-4-imidazolyl)methyl-1H-indazole-3-methanol

Product 1

HCID 154286393-Chloromethyl-5,6-dimethoxy-1-(1-trityl-4-imidazolyl)methyl-1H-indazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5,6-Dimethoxy-1(1-trityl-4-imidazolyl)methyl-1H -indazole-3-methanol (180.0 g), which had been ground in a mortar, was suspended in dichloromethane (1700 ml) at room temperature and then cooled with ice/water. Next, thionyl chloride (48.6 ml) was dropped thereinto within 5 minutes. The reaction mixture was poured into a saturated aqueous solution of sodium bicarbonate (2000 ml) and extracted with chloroform (5000 ml). After drying over sodium sulfate, filtering and evaporating under reduced pressure, a colorless solid was obtained (165.1 g). This solid product was used in the subsequent reaction without purification.

Workup

  1. extractionextracted with chloroform (5000 ml)
  2. dry with materialAfter drying over sodium sulfate
  3. filtrationfiltering
  4. customevaporating under reduced pressure
  5. customa colorless solid was obtained (165.1 g)
  6. customThis solid product was used in the subsequent reaction without purification

Sources & evidence

ORD record
ord-7f513d419ab44e8b803173fa8555b14d
Source dataset
uspto-grants-1997_08
Patent number
US05661150

Reaction notes

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