Triethylamine → HCID 10853462, compound

HRID 2210881Notes

Reaction equation

HRID 2210881 reaction equation
[NH:1]1[C:5]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N:4][N:3]=[N:2]1.C(N(CC)CC)C.Br[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>C(#N)C>[CH2:31]([N:3]1[N:2]=[N:1][C:5]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N:4]1)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH3:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 89191-BromododecaneHCID 178470801HCID 178470801, compound2×

Product 1

HCID 10853462HCID 10853462, compoundYield 49.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
24 °C

Procedure

The tetrazoleacetic acid, ethyl ester (50 g, 0.26 tool) obtained in (a) was suspended in acetonitrile (600 mL) and triethylamine (52.4 g, 0.52 tool)was added in one portion. The solution was heated at reflux for 5 minutes, cooled to 24° C., and then treated dropwise with 1-bromododecane (64.5 g, 0.26 mol). The solution was refluxed overnight, cooled, and the solvent concentrated in vacuo. The residue was triturated with ethyl acetate (300 mL), filtered, and the filtrate was washed with aqueous HCl (1M), brine, dried (MgSO4), and filtered. The filtrate was concentrated in vacuo leaving a viscous liquid. The 2-isomer was separated from the crude mixture using silica gel chromatography (elution with 25% EtOAc/75% hexane), isolating 2-dodecyltetrazoleacetic acid, ethyl ester (41.8 g, 49%) as a pale yellow liquid.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 5 minutes
  3. temperatureThe solution was refluxed overnight
  4. temperaturecooled
  5. concentrationthe solvent concentrated in vacuo
  6. customThe residue was triturated with ethyl acetate (300 mL)
  7. filtrationfiltered
  8. washthe filtrate was washed with aqueous HCl (1M), brine
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. concentrationThe filtrate was concentrated in vacuo
  12. customleaving a viscous liquid
  13. customThe 2-isomer was separated from the crude mixture
  14. washsilica gel chromatography (elution with 25% EtOAc/75% hexane)

Sources & evidence

ORD record
ord-704477f9e29942b5b8a3396e12574d4d
Source dataset
uspto-grants-1995_10
Patent number
US05461049

Reaction notes

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