2,6-Diisopropylphenyl isocyanate → N-[2,6-bis(1-methylethyl)phenyl]-N'-(3-dodecyl-5-isoxazolyl)urea
Reaction equation
[NH2:1][C:2]1[O:6][N:5]=[C:4]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:3]=1.[CH:19]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH:28]([CH3:30])[CH3:29])[C:23]=1[N:31]=[C:32]=[O:33])([CH3:21])[CH3:20]>C(#N)C>[CH3:21][CH:19]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH:28]([CH3:29])[CH3:30])[C:23]=1[NH:31][C:32]([NH:1][C:2]1[O:6][N:5]=[C:4]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:3]=1)=[O:33])[CH3:20]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
A slurry of 5-amino-3-dodecylisoxazole (1.44 g, 5.71 mmol) in acetonitrile (50 mL) was warmed until homogeneous. 2,6-Diisopropylphenylisocyanate (1.22 mL, 5.71 mmol) was then added in one portion and the resulting solution was heated under reflux for 24 hours. The resulting solution was cooled to -20° C. The resulting precipitate was collected by filtration, dissolved in a minimal amount of warm chloroform, and chromatographed on silica (70:30 hexane:ethyl acetate). The product containing fractions were concentrated and the resulting solid was recrystallized from acetonitrile to yield 0.53 g (20.4%) of the title compound as white needles, m.p. 112.5°-114° C.
Workup
- temperaturethe resulting solution was heated
- temperatureunder reflux for 24 hours
- filtrationThe resulting precipitate was collected by filtration
- dissolutiondissolved in a minimal amount of warm chloroform
- customchromatographed on silica (70:30 hexane:ethyl acetate)
- additionThe product containing fractions
- concentrationwere concentrated
- customthe resulting solid was recrystallized from acetonitrile
Sources & evidence
- ORD record
- ord-9d7f0db8673f42509d1192b37eac2445
- Source dataset
- uspto-grants-1992_11
- Patent number
- US05162360
Reaction notes
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