Imidazole → 5-(1H-imidazol-1-yl)-7,8-dihydronaphthalene-2-carbonitrile

HRID 1591074Notes

Reaction equation

HRID 1591074 reaction equation
S(Cl)(Cl)=O.[NH:5]1[CH:9]=[CH:8][N:7]=[CH:6]1.[C:10]([C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[C:18](=O)[CH2:17][CH2:16][CH2:15]2)#[N:11].C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.O>[C:10]([C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[C:18]([N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1)=[CH:17][CH2:16][CH2:15]2)#[N:11]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 108991325-Oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

Product 1

HCID 98373925-(1H-imidazol-1-yl)-7,8-dihydronaphthalene-2-carbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

175 μl of thionyl chloride are added dropwise to a solution of 272 mg of imidazole in 2.5 ml of methylene chloride. 342 mg of 6-cyano-1-tetralone are added in portions to the resulting white suspension, and the reaction mixture is stirred for 7 hours at 40° and then for 24 hours at room temperature. 386 mg of potassium carbonate in 1.6 ml of water are added to the reaction mixture, which is then extracted with chloroform. After drying the organic phase over sodium sulfate, concentration is carried out under reduced pressure. The resulting crude product is purified by column chromatography (0.04-0.063 mesh SIO2, hexane/ethyl acetate 1:2). Crystallisation from ether yields the title compound in the form of colourless crystals; m.p. 152°-153°. TLC (ethyl acetate): Rf=0.17.

Workup

  1. waitfor 24 hours at room temperature
  2. extractionis then extracted with chloroform
  3. customAfter drying the organic phase
  4. concentrationover sodium sulfate, concentration
  5. customThe resulting crude product is purified by column chromatography (0.04-0.063 mesh SIO2, hexane/ethyl acetate 1:2)
  6. customCrystallisation from ether

Sources & evidence

ORD record
ord-fcd1697a45a348e9ba48221609987dbe
Source dataset
uspto-grants-1993_04
Patent number
US05206256

Reaction notes

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