2,6-Diisopropylphenyl isocyanate → HCID 19780331, compound

HRID 2081655Notes

Reaction equation

HRID 2081655 reaction equation
[NH2:1][C:2]1[N:3]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[N:4]=[CH:5][N:6]=1.[CH:18]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH:27]([CH3:29])[CH3:28])[C:22]=1[N:30]=[C:31]=[O:32])([CH3:20])[CH3:19]>C1COCC1>[CH3:20][CH:18]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH:27]([CH3:28])[CH3:29])[C:22]=1[NH:30][C:31]([NH:1][C:2]1[N:3]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[N:4]=[CH:5][N:6]=1)=[O:32])[CH3:19]

Participants

4

Reactant 2

HCID 922592,6-Diisopropylphenyl isocyanateHCID 10610009HCID 10610009, compound

Product 1

HCID 19780331HCID 19780331, compoundYield 37.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 3-amino-2-undecyl-1,2,4-triazole (3.0 g, 12.6 mmol) and 2,6-diisopropylphenyl isocyanate (3.9 mL, 19.2 mmol) in THF (100 mL) was heated under reflux (40 hours). The resulting solution was cooled (25° C.) and concentrated in vacuo. The resulting oil was triturated with hexane and the resulting solid was collected by filtration and recrystallized from hot hexane to yield 2.1 g (37.8%) of the title compound as a white solid; mp 146.5°-147.5° C.

Workup

  1. temperatureunder reflux (40 hours)
  2. concentrationconcentrated in vacuo
  3. customThe resulting oil was triturated with hexane
  4. filtrationthe resulting solid was collected by filtration
  5. customrecrystallized from hot hexane

Sources & evidence

ORD record
ord-5947d646494f4579a55d749d0526601e
Source dataset
uspto-grants-1993_02
Patent number
US05185358

Reaction notes

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