Water → HCID 90427081, compound

HRID 2278956Notes

Reaction equation

[CH3:1][C:2](=[CH2:5])[CH2:3][NH2:4].C1CCN2C(=NCCC2)CC1.[CH:17]1([N:23]=[C:24]=[O:25])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.O>O1CCOCC1>[CH:17]1([NH:23][C:24]([NH:4][CH2:3][C:2]([CH3:1])=[CH2:5])=[O:25])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 2-methylallylamine (0.156 g, 2.197 mmol) in dioxane (5 mL) was treated with DBU (0.030 mL, 0.200 mmol) and cyclohexyl isocyanate (0.25 g, 1.997 mmol) and heated at 60° C. overnight. The mixture was cooled to RT, treated with water, extracted with EtOAc (2×) and the combined organics were washed with brine, dried over Na2SO4 and concentrated to dryness to afford 1-cyclohexyl-3-(2-methylallyl)urea (340 mg, 87%). 1H NMR (400 MHz, DMSO-d6): δ 5.80 (m, 1 H), 5.72 (d, J=8.0 Hz, 1 H), 4.72 (m, 1 H), 4.68 (m, 1 H), 3.50 (d, J=5.3 Hz, 2 H), 3.30 (m, 1 H), 1.70 (m, 2 H), 1.61 (s, 3 H), 1.60 (m, 1 H), 1.48 (m, 1 H), 1.27 (m, 2 H), 1.13 (m, 4 H); MS (ESI) m/z: 197.2 (M+H+).

Workup

temperatureThe mixture was cooled to RT
extractionextracted with EtOAc (2×)
washthe combined organics were washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-cb013e7cfcb544909d6c6d1f9e0c1543
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133183B2

Reaction notes

Loading…