Potassium Iodide → 1-Cyano-4-(2-tetrazolyl)methyl-naphthalene

HRID 1461083Notes

Reaction equation

HRID 1461083 reaction equation
[NH:1]1[CH:5]=[N:4][N:3]=[N:2]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[C:14]([C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]([CH2:26]Br)=[CH:18][CH:17]=1)#[N:15]>CC(C)=O>[C:14]([C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]([CH2:26][N:2]2[N:3]=[N:4][CH:5]=[N:1]2)=[CH:18][CH:17]=1)#[N:15]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 124330084-(Bromomethyl)naphthalene-1-carbonitrileHCID 178418441HCID 178418441, compound

Product 1

HCID 199814561-Cyano-4-(2-tetrazolyl)methyl-naphthalene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

420 mg of tetrazole, 553 mg of potassium carbonate and 53 mg of potassium iodide are added to a solution of 985 mg of 1-cyano-4-bromomethyl-naphthalene in 20 ml acetone, and the mixture is stirred for 3.5 hours at 45°. After the reaction mixture has cooled, the solvent is distilled off and the residue is dissolved in methylene chloride. The organic solution is washed with water and brine, then dried over sodium sulfate and concentrated. Separation by column chromatography yields first, by elution with toluene/ethyl acetate (9:1), 1-cyano-4-(2-tetrazolyl)methyl-naphthalene, m.p. 124°, [IR(CH2Cl2): 3052, 2225, 1592, 1516 cm-1, 1H-NMR (DMSO-d6): δ=6.62 (2H, s), 7.6 and 8.2 (2H, m), 7.83 (2H, m), 8.2 and 8.33 (2H, m), 9.02 (1H, s) ppm] and then, with toluene/ethyl acetate (3:1), 1-cyano- 4-(1-tetrazolyl)methylnaphthalene, m.p. 171° [IR(CH2Cl2): 3050, 2227, 1516, 1482 cm-1 ; 1H-NMR (DMSO-d6): δ=6.36 (2H, s), 7.5 and 8.2 (2H, m), 7.85 (2H, m), 8.2 and 8.37 (2H, m), 9.6 (1H, s) ppm.

Workup

  1. temperatureAfter the reaction mixture has cooled
  2. distillationthe solvent is distilled off
  3. dissolutionthe residue is dissolved in methylene chloride
  4. washThe organic solution is washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customSeparation by column chromatography

Sources & evidence

ORD record
ord-7e65a05f175a418caacd5551ba81cfad
Source dataset
uspto-grants-1991_12
Patent number
US05073574

Reaction notes

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