Hexane → HCID 15512312, compound

HRID 1490335Notes

Reaction equation

HRID 1490335 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[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=1)[N:7]=[C:6]2[CH2:25]O.S(Cl)([Cl:29])=O.C(OCC)(=O)C.CCCCCC>ClCCl>[Cl:29][CH2:25][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[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=2)[N:7]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 24386Thionyl ChlorideHCID 15512311HCID 15512311, compound

Product 1

HCID 15512312HCID 15512312, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In 1500 ml of dichloromethane was dissolved 184.0 g of 5,6-dimethoxy-1-(3,4-dimethoxybenzyl)-3-hydroxymethyl-1H-indazole at room temperature, followed by stirring under cooling with ice. To the solution was added dropwise 75.4 ml of thionyl chloride over 20 minutes. One minute later, the spot of the starting material on a thin layer chromatogram (ethyl acetate:hexane=2:1) disappeared. The reaction mixture was warmed to room temperature, and 3500 ml of dichloromethane was added thereto. The mixture was washed with 1000 ml of a saturated sodium Hydrogencarbonate aqueous solution, dried over sodium sulfate, filtered, and the evaporation of the solvent gave 189.7 g of a colorless solid. This solid was used in the subsequent reaction without further purification.

Workup

  1. temperatureunder cooling with ice
  2. customOne minute
  3. washThe mixture was washed with 1000 ml of a saturated sodium Hydrogencarbonate aqueous solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customthe evaporation of the solvent

Sources & evidence

ORD record
ord-38259609af4442e3bbe7636a4dc097a1
Source dataset
uspto-grants-1997_10
Patent number
US05681954

Reaction notes

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