Triethylamine → HCID 10668716, compound

HRID 1756901Notes

Reaction equation

HRID 1756901 reaction equation
[C:1]1([CH:7]([C:13]2[NH:17][N:16]=[N:15][N:14]=2)[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Br[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]>C(#N)C>[CH2:37]([N:15]1[N:16]=[N:17][C:13]([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N:14]1)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH3:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 89191-BromododecaneHCID 178470659HCID 178470659, compound

Product 1

HCID 10668716HCID 10668716, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The tetrazole ester (a) (47 g; 0.20 moles) was dissolved in acetonitrile (550 mL) containing one equivalent of triethylamine (20.2 g; 0.20 moles). The solution was heated to reflux and then 1-bromododecane (49.8 g; 0.20 moles) was added dropwise over 20 minutes. Upon completion, the solution was heated to reflux for 16 hours, cooled to room temperature, and concentrated in vacuo. The residue was triturated with ethyl acetate (1 L), filtered, and the filtrate was washed with aqueous HCl (1N), brine, and dried over magnesium sulfate. The drying agent was removed by filtration and the solvent concentrated in vacuo, leaving a viscous liquid containing both 1- and 2-isomers. The regioisomers were separated by silica gel chromatography using 75% hexane and 25% ethyl acetate as the eluent, obtaining the title compound as a colorless liquid. Yield: 33 g (41%).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux
  3. temperatureUpon completion, the solution was heated
  4. temperatureto reflux for 16 hours
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with ethyl acetate (1 L)
  7. filtrationfiltered
  8. washthe filtrate was washed with aqueous HCl (1N), brine
  9. dry with materialdried over magnesium sulfate
  10. customThe drying agent was removed by filtration
  11. concentrationthe solvent concentrated in vacuo
  12. customleaving a viscous liquid
  13. additioncontaining both 1- and 2-isomers
  14. customThe regioisomers were separated by silica gel chromatography

Sources & evidence

ORD record
ord-4dc41c78894e4c07b3dba9391591da88
Source dataset
uspto-grants-1995_08
Patent number
US05441975

Reaction notes

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