Triethylamine → 1-(2,6-Diisopropyl-phenyl)-3-(5-tridecyl-[1,3,4]oxadiazol-2-yl)-urea

HRID 2081663Notes

Reaction equation

HRID 2081663 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[O:10][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[N:12][N:13]=1.[CH:27]([C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([CH:36]([CH3:38])[CH3:37])[C:31]=1[N:39]=[C:40]=[O:41])([CH3:29])[CH3:28]>C(#N)C>[CH3:29][CH:27]([C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([CH:36]([CH3:37])[CH3:38])[C:31]=1[NH:39][C:40]([NH:8][C:9]1[O:10][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[N:12][N:13]=1)=[O:41])[CH3:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 922592,6-Diisopropylphenyl isocyanateHCID 105879212-Amino-5-tridecyl-1,3,4-oxadiazole

Product 1

HCID 106480641-(2,6-Diisopropyl-phenyl)-3-(5-tridecyl-[1,3,4]oxadiazol-2-yl)-urea

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Triethylamine (1.67 g, 0.017 mol) was added to a solution of the compound prepared in Step 2 above (4.0 g, 0.015 mol) in acetonitrile (200 mL) and the mixture refluxed for 30 minutes or until solution becomes homogeneous. 2,6-Diisopropylphenyl isocyanate (3.71 g, 0.018 mol) was then added and reflux continued for 18 hours. The mixture was allowed to cool, concentrated, diluted with water (20 mL), filtered, and the solid columned on silica gel, eluting with 20% ethyl acetate in hexanes (loaded in chloroform) to give 0.54 g of a solid; m.p 114°-116.5° C.

Workup

  1. temperaturethe mixture refluxed for 30 minutes or until solution
  2. temperaturereflux
  3. temperatureto cool
  4. concentrationconcentrated
  5. additiondiluted with water (20 mL)
  6. filtrationfiltered
  7. washthe solid columned on silica gel, eluting with 20% ethyl acetate in hexanes (loaded in chloroform)

Sources & evidence

ORD record
ord-1888fc7206f54f62a49636f9af4733d4
Source dataset
uspto-grants-1993_02
Patent number
US05185358

Reaction notes

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