Imidazole → HCID 14349630, compound

HRID 329941Notes

Reaction equation

HRID 329941 reaction equation
S(Cl)(Cl)=O.[NH:5]1[CH:9]=[CH:8][N:7]=[CH:6]1.[OH:10][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:20]=1[C:19](=O)[CH2:18][CH2:17][CH2:16]2>C(Cl)Cl>[N:5]1([C:19]2[C:20]3[C:15](=[CH:14][CH:13]=[CH:12][C:11]=3[OH:10])[CH2:16][CH2:17][CH:18]=2)[CH:9]=[CH:8][N:7]=[CH:6]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24386Thionyl ChlorideHCID 5843538-Hydroxy-3,4-dihydronaphthalen-1(2H)-one

Product 1

HCID 14349630HCID 14349630, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

227 g (1.9 mols) of thionyl chloride are added dropwise to a mixture of 503 g (7.4 mols) of imidazole and 1.6 liter of methylene chloride at 5° C., while stirring. The mixture is subsequently stirred for 20 minutes and 157 g (0.97 mol) of 8-hydroxy-1-tetralone are then added. The reaction mixture is stirred for a further 2 hours and then filtered and the filtrate is poured into ice water. The organic phase is separated off and concentrated under reduced pressure. The residue is taken up in 1 liter of toluene and the solution formed is boiled under reflux for one hour. The mixture is concentrated again under reduced pressure and the residue which remains is dissolved in methylene chloride. The organic phase is washed with water and concentrated under reduced pressure. The residue is triturated with toluene, the product separating out as crystals. 95 g of 3,4-dihydro-1-(imidazol-1-yl)-8-hydroxynaphthalene of melting point 186° C. are obtained in this manner.

Workup

  1. stirringThe mixture is subsequently stirred for 20 minutes
  2. stirringThe reaction mixture is stirred for a further 2 hours
  3. filtrationfiltered
  4. additionthe filtrate is poured into ice water
  5. customThe organic phase is separated off
  6. concentrationconcentrated under reduced pressure
  7. customthe solution formed
  8. temperatureunder reflux for one hour
  9. concentrationThe mixture is concentrated again under reduced pressure
  10. dissolutionthe residue which remains is dissolved in methylene chloride
  11. washThe organic phase is washed with water
  12. concentrationconcentrated under reduced pressure
  13. customThe residue is triturated with toluene
  14. customthe product separating out as crystals

Sources & evidence

ORD record
ord-192c239eb6754f048f2f3293a34a0479
Source dataset
uspto-grants-1990_01
Patent number
US04894381

Reaction notes

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