Acetonitrile → 4-(2-Pyridylmethyl)-2-dodecyl-2H-tetrazole

HRID 1756911Notes

Reaction equation

HRID 1756911 reaction equation
N1C=CC=CC=1C[C:8]1[NH:12][N:11]=[N:10][N:9]=1.C([N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])C.Br[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].[C:33](#N)[CH3:34]>CCCCCC>[N:15]1[CH:16]=[CH:17][CH:34]=[CH:33][C:18]=1[CH2:19][N:9]1[CH:8]=[N:12][N:11]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[NH:10]1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 89191-BromododecaneHCID 178420215HCID 178420215, compound

Product 1

HCID 214695704-(2-Pyridylmethyl)-2-dodecyl-2H-tetrazole

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

The tetrazole (a) (3.0 g; 0. 015 moles) was taken up in acetonitrile (50 mL) containing two equivalents of triethylamine (3.0 g; 0.030 moles). The suspension was heated to reflux and then treated with 1-bromododecane (3.7 g; 0.015 moles) dropwise for several minutes. The solution was refluxed for 16 hours, cooled to room temperature, and the solvent removed in vacuo. The residue was triturated with ethyl acetate, filtered, and concentration of the filtrate in vacuo leaving a maroon-colored liquid. The 2-isomer was obtained by dissolving the crude product in 50% hexane/50% ethyl acetate and removing the impurities, including the 1-regioisomer, by silica gel chromatography. Yield: 2.0 g (41%).

Workup

  1. temperatureThe suspension was heated
  2. temperatureto reflux
  3. temperatureThe solution was refluxed for 16 hours
  4. customthe solvent removed in vacuo
  5. customThe residue was triturated with ethyl acetate
  6. filtrationfiltered
  7. customconcentration of the filtrate in vacuo leaving a maroon-colored liquid
  8. customThe 2-isomer was obtained
  9. customremoving the impurities

Sources & evidence

ORD record
ord-ca87683a93f24f3e9232d005637bcdab
Source dataset
uspto-grants-1995_08
Patent number
US05441975

Reaction notes

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