Triethylamine → HCID 10766242, compound

HRID 1460998Notes

Reaction equation

HRID 1460998 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[N:13]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[N:12]=[N:11][N:10]=1.[CH:26]([C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([CH:35]([CH3:37])[CH3:36])[C:30]=1[N:38]=[C:39]=[O:40])([CH3:28])[CH3:27]>C(#N)C>[CH3:28][CH:26]([C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([CH:35]([CH3:36])[CH3:37])[C:30]=1[NH:38][C:39]([NH:8][C:9]1[N:13]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[N:12]=[N:11][N:10]=1)=[O:40])[CH3:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 922592,6-Diisopropylphenyl isocyanateHCID 10515057HCID 10515057, compound

Product 1

HCID 10766242HCID 10766242, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Triethylamine (2.50 mL, 18.0 mmol) was added to a slurry of 5-amino-1-dodecyltetrazole (4.56 g, 18.0 mmol) in acetonitrile (150 mL). The mixture was heated to reflux and upon dissolution of the solid, 2,6-diisopropylphenyl isocyanate (3.90 mL, 18.1 mmol) was added in one portion. The solution was refluxed for 18 hours and allowed to cool. The resultant precipitate was filtered and the filtrate concentrated in vacuo and partitioned between ethyl acetate and water (1:1). The organic layer was washed with brine, dried over Na2SO4, filtered, concentrated in vacuo, and columned on silica gel, eluting with 10% then 15% ethyl acetate in hexanes to give an oil which solidified on standing to give the title compound as a white solid (1.95 g, 24%), m.p. 80-88° C.

Workup

  1. temperatureThe mixture was heated
  2. additionwas added in one portion
  3. temperatureThe solution was refluxed for 18 hours
  4. temperatureto cool
  5. filtrationThe resultant precipitate was filtered
  6. concentrationthe filtrate concentrated in vacuo
  7. custompartitioned between ethyl acetate and water (1:1)
  8. washThe organic layer was washed with brine
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. washeluting with 10%
  13. custom15% ethyl acetate in hexanes to give an oil which

Sources & evidence

ORD record
ord-4e7347edd2744f4ab7a308943fc280b2
Source dataset
uspto-grants-1991_12
Patent number
US05073565

Reaction notes

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