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

HRID 1490341Notes

Reaction equation

HRID 1490341 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(Cl)(Cl)Cl.C(=O)([O-])O.[Na+]>ClCCl.C(O)C>[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

7

Reactant 4

HCID 6212ChloroformHCID 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 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

In 1700 ml of dichloromethane was suspended 180.0 g of 5,6-dimethoxy-1-(1-trityl-4-imidazolyl)methyl-1H-indazole-3-methanol, having been ground to powder in a mortar, at room temperature, followed by stirring while cooling with ice. To the reaction mixture was added dropwise 48.6 ml of thionyl chloride over 5 minutes. One minute later, the spot of the starting material on a thin layer chromatogram (chloroform:ethanol=30:1) disappeared. The reaction mixture was poured into 2000 ml of a saturated sodium hydrogencarbonate aqueous solution and extracted with 5000 ml of chloroform. The extract was dried over sodium sulfate, filtered, and the solvent was evaporated to yield 165.1 g of a colorless solid. This solid was used in the subsequent reaction without further purification.

Workup

  1. customat room temperature
  2. temperaturewhile cooling with ice
  3. customOne minute
  4. extractionextracted with 5000 ml of chloroform
  5. dry with materialThe extract was dried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-796744cd44e94a93b708ad5e579c7971
Source dataset
uspto-grants-1997_10
Patent number
US05681954

Reaction notes

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