2,6-Diisopropylphenyl isocyanate → HCID 19780333, compound

HRID 2081652Notes

Reaction equation

HRID 2081652 reaction equation
[C:1]([N:4]1[C:8]([NH2:9])=[N:7][C:6]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[N:5]1)(=[O:3])[CH3:2].[CH:21]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]([CH3:32])[CH3:31])[C:25]=1[N:33]=[C:34]=[O:35])([CH3:23])[CH3:22]>>[CH3:23][CH:21]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]([CH3:31])[CH3:32])[C:25]=1[NH:33][C:34]([NH:9][C:8]1[N:4]([C:1](=[O:3])[CH3:2])[N:5]=[C:6]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[N:7]=1)=[O:35])[CH3:22]

Participants

3

Reactant 2

HCID 922592,6-Diisopropylphenyl isocyanateHCID 19780329HCID 19780329, compound

Product 1

HCID 19780333HCID 19780333, compoundYield 66.3%

Conditions

Temperature
20 °C

Procedure

A slurry of 1-acetyl-5-amino-3-undecyl-1,2,4-triazole (3.56 g, 12.7 mmol) was warmed until homogeneous. 2,6-Diisopropylphenyl isocyanate (2.71 mL, 12.7 mmol) was added and the resulting solution was heated under reflux for 15 hours. The resulting solution was cooled (20° C.) and the precipitate was removed by filtration. The filtrate was concentrated in vacuo and the resulting oil was chromatographed on silica (85:15 hexane:ethyl acetate) to yield 4.07 g (66.3%) of the title compound as a light yellow oil.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureunder reflux for 15 hours
  3. customthe precipitate was removed by filtration
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe resulting oil was chromatographed on silica (85:15 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-da5c26eff0c64e4f993fa73bc9ffb585
Source dataset
uspto-grants-1993_02
Patent number
US05185358

Reaction notes

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