Tin tetrachloride → HCID 12832389, compound

HRID 1995232Notes

Reaction equation

HRID 1995232 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[CH:11][NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.[O:22]1[CH:26]=[CH:25][CH2:24][CH2:23]1.[Sn](Cl)(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>ClCCCl>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]2[N:12]=[CH:11][N:10]([CH:23]3[CH2:24][CH2:25][CH2:26][O:22]3)[C:9]=2[C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 24287Tin tetrachlorideHCID 709342,3-DihydrofuranHCID 516892Sodium BicarbonateHCID 14100143HCID 14100143, compound

Product 1

HCID 12832389HCID 12832389, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

5.61 g of 4,5-bis(4-methoxyphenyl)imidazole is suspended in 150 ml of absolute 1,2-dichloroethane and combined with 2.8 g of 2,3-dihydrofuran as well as 0.2 ml of tin tetrachloride. The mixture is heated under agitation for 12 hours to 70°, allowed to cool, and poured into 200 ml of cold sodium bicarbonate solution. The organic phase is separated, dried over sodium sulfate, and concentrated under vacuum. The residue is dissolved in dichloromethane and subjected to a hexane precipitation. The precipitate is subjected to column chromatography on 250 g of aluminum oxide, neutral, activity stage II. Elution with ethyl acetate/hexane 2:3 yields 5.39 g of 4,5-bis(4-methoxyphenyl)-1-(tetrahydrofuran-2-yl)imidazole, which is obtained in the form of a foam after removal of the solvent.

Workup

  1. temperatureThe mixture is heated under agitation for 12 hours to 70°
  2. temperatureto cool
  3. customThe organic phase is separated
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. dissolutionThe residue is dissolved in dichloromethane
  7. customsubjected to a hexane precipitation
  8. washElution with ethyl acetate/hexane 2:3

Sources & evidence

ORD record
ord-aa176a5a87e4462485693beef473e119
Source dataset
uspto-grants-1983_09
Patent number
US04402960

Reaction notes

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