Imidazole → 1-(6-Chloro-3,4-dihydronaphthalen-1-yl)-1H-imidazole

HRID 1591075Notes

Reaction equation

HRID 1591075 reaction equation
S(Cl)(Cl)=O.[NH:5]1[CH:9]=[CH:8][N:7]=[CH:6]1.[Cl:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[C:17](=O)[CH2:16][CH2:15][CH2:14]2.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.O>[Cl:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[C:17]([N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1)=[CH:16][CH2:15][CH2:14]2

Participants

7

Reactant 4

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 122911496-Chloro-1-tetralone

Product 1

HCID 233653621-(6-Chloro-3,4-dihydronaphthalen-1-yl)-1H-imidazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

0.218 ml of thionyl chloride is added within a period of 15 minutes to a solution of 815 mg of imidazole in 3.2 ml of methylene chloride. At the end of the exothermic reaction, 451 mg of 6-chloro-1-tetralone are added to the resulting suspension. After stirring for 20 hours at room temperature, 497 mg of potassium carbonate in 2 ml of water are added, and the mixture is extracted twice with chloroform. After drying the organic extracts over sodium sulfate, concentration is carried out under reduced pressure. The resulting crude product is purified by column chromatography (SiO2, 0.04-0.063 mesh, 0.15 bar, ethyl acetate); m.p. (after dry crystallisation from ether) 68°-72°.

Workup

  1. additionare added to the resulting suspension
  2. extractionthe mixture is extracted twice with chloroform
  3. customAfter drying the organic extracts
  4. concentrationover sodium sulfate, concentration
  5. customThe resulting crude product is purified by column chromatography (SiO2, 0.04-0.063 mesh, 0.15 bar, ethyl acetate)
  6. dry with materialm.p. (after dry crystallisation from ether) 68°-72°

Sources & evidence

ORD record
ord-782dfac174ce446899055ac0ec25a492
Source dataset
uspto-grants-1993_04
Patent number
US05206256

Reaction notes

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