2,6-Diisopropylphenyl isocyanate → N-[2,6-bis(1-methylethyl)phenyl]-N'-(5-dodecyl-3-isoxazolyl)urea

HRID 373171Notes

Reaction equation

[NH2:1][C:2]1[CH:6]=[C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[O:4][N: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[CH:6]=[C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[O:4][N:3]=1)=[O:33])[CH3:20]

Participants

Conditions

Temperature: 25 °C

Procedure

A slurry of 3-amino-5-dodecylisoxazole (2.20 g, 8.72 mmol) in acetonitrile (50 mL) was warmed until homogeneous. 2,6-Diisopropylphenyl-isocyanate (1.86 mL, 8.72 mmol) was then added in one portion and the resulting solution was heated under reflux for 6 hours. The resulting solution was cooled (25° C.), concentrated in vacuo, and chromatographed on silica (90:10 to 70;30 hexane:ethyl acetate). The product containing fractions were combined and concentrated to a solid which was washed with cold acetonitrile to yield 0.95 g (23.9%) of the title compound as a white solid, m.p. 101°-107° C.

Workup

temperaturethe resulting solution was heated
temperatureunder reflux for 6 hours
concentrationconcentrated in vacuo
customchromatographed on silica (90:10 to 70;30 hexane:ethyl acetate)
additionThe product containing fractions
concentrationconcentrated to a solid which
washwas washed with cold acetonitrile

Sources & evidence

ORD record: ord-0c82ac704cbc4201a3832dedeafa61b7
Source dataset: uspto-grants-1992_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05162360

Reaction notes

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