Potassium Iodide → HCID 23365331, compound

HRID 1461082Notes

Reaction equation

HRID 1461082 reaction equation
[NH:1]1[CH:5]=[N:4][N:3]=[N:2]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Br[CH2:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=1>CC(C)=O>[N:1]1[N:2]([CH2:15][C:16]2[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=2)[N:3]=[N:4][CH:5]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 869964-(Bromomethyl)benzonitrileHCID 178418441HCID 178418441, compound

Product 1

HCID 23365331HCID 23365331, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

6.3 g of tetrazole, 8.28 g of potassium carbonate and 0.675 g of potassium iodide are added in succession to a solution of 12 g of 4-bromomethylbenzonitrile in 400 ml of acetone and the mixture is then stirred for 19 hours at 40°-45°. The reaction mixture is cooled, filtered and concentrated. The residue is partitioned between CH2Cl2 and water. The organic phase is washed with brine, dried over sodium sulfate and then concentrated by evaporation. Subsequent chromatography (silica gel) yields first, with toluene/ethyl acetate (2:1), 4-(2-tetrazolyl)methyl-benzonitrile [TLC (hexane/ethyl acetate, 1:2) Rf =0.76); 1H-NMR (CDCl3): δ=5.8 (2H, s), 7.4 and 7.7 (4H, m), 8.5 (1H, s) ppm], and then, with ethyl acetate, 4-(1-tetrazolyl)methyl-benzonitrile [TLC (hexane/ethyl acetate, 1:2), Rf =0.36); 1H-NMR (CDCl3): δ=5.63 (2H, s), 7.4 and 7.7 (4H, m), 8.6 (1H, s) ppm].

Workup

  1. temperatureThe reaction mixture is cooled
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe residue is partitioned between CH2Cl2 and water
  5. washThe organic phase is washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-09f3aceb3ca64bf7a875ccc30e0a6388
Source dataset
uspto-grants-1991_12
Patent number
US05073574

Reaction notes

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