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

HRID 617630Notes

Reaction equation

HRID 617630 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)C.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

6

Reactant 4

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 154286385,6-dimethoxy-1-(1-trityl-4-imidazolyl)methyl-1H-indazole-3-methanolHCID 21889567Chloroform ethanol

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) was ground into a powder form using a mortar and suspended in dichloromethane (1,700 ml) at room temperature. After suspension, the reaction solution was stirred with cooling in an ice bath. To this was added dropwise 48.6 ml of thionyl chloride spending 5 minutes. It was observed 1 minute thereafter that the spot of the material almost disappeared on a thin layer chromatography (chloroform/ethanol=30/1). The reaction solution was poured into saturated sodium bicarbonate aqueous solution (2,000 ml) and extracted with chloroform (5,000 ml), and the extract was dried with sodium sulfate, filtered and then evaporated under a reduced pressure to obtain colorless solid (165.1 g). This solid substance was used in the subsequent reaction as such.

Workup

  1. temperaturewith cooling in an ice bath
  2. extractionextracted with chloroform (5,000 ml)
  3. dry with materialthe extract was dried with sodium sulfate
  4. filtrationfiltered
  5. customevaporated under a reduced pressure

Sources & evidence

ORD record
ord-01fda1a5764a4ddc9b03174ac6869a51
Source dataset
uspto-grants-1999_09
Patent number
US05948913

Reaction notes

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