3-Aminophenol → 1-(5-Tert-butylisoxazol-3-yl)-3-(3-hydroxyphenyl)urea

HRID 631181Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[C:9]([C:13]1[O:17][N:16]=[C:15]([N:18]=[C:19]=[O:20])[CH:14]=1)([CH3:12])([CH3:11])[CH3:10]>C1COCC1>[C:9]([C:13]1[O:17][N:16]=[C:15]([NH:18][C:19]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[CH:3]=2)=[O:20])[CH:14]=1)([CH3:12])([CH3:10])[CH3:11]

Participants

Conditions

Temperature: 50 °C

Procedure

to THF (300 ml, degassed w/ argon) was added 3-aminophenol (4.36 g, 40 mmol) and 5-tert-butyl-3-isocyanatoisoxazole (6.64 g, 40 mmol) and the mixture was heated at 50° C. overnight. After cooling to room temperature, the reaction was concentrated in vacuo, and the resulting foam purified by column chromatography (25-75% EtOAc/hexanes) to give 1-(5-tert-butylisoxazol-3-yl)-3-(3-hydroxyphenyl)urea (8.81 g, 32 mmol, 80%). 1H NMR (300 MHz, DMSO-d6) δ 9.39 (s, 1h), 9.37 (s, 1h), 8.69 (s, 1h), 7.06 (t, 1h), 7.01 (s, 1h), 6.78 (d, 1h), 6.49 (s, 1h), 6.41 (d, 1h), 1.29 (s, 9h); LC-MS (ESI) m/z 275 (M+H)+.

Workup

temperatureAfter cooling to room temperature
concentrationthe reaction was concentrated in vacuo
customthe resulting foam purified by column chromatography (25-75% EtOAc/hexanes)

Sources & evidence

ORD record: ord-a574c6ac14b64649aec75f41bb31c534
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09320739B2

Reaction notes

Loading…