Ethanolamine → N-((Z)-2-(4-Chlorophenyl)-1-{[(2-hydroxyethyl)amino]carbonyl}vinyl)-4-[2-(4-methoxyphenyl)ethoxy]benzamide

HRID 456269Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][OH:4].[Cl:5][C:6]1[CH:35]=[CH:34][C:9](/[CH:10]=[C:11]2\[N:12]=[C:13]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][C:26]4[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=4)=[CH:19][CH:18]=3)[O:14][C:15]\2=[O:16])=[CH:8][CH:7]=1>C(O)C>[Cl:5][C:6]1[CH:7]=[CH:8][C:9](/[CH:10]=[C:11](\[NH:12][C:13](=[O:14])[C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][C:26]3[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=3)=[CH:19][CH:18]=2)/[C:15]([NH:1][CH2:2][CH2:3][OH:4])=[O:16])=[CH:34][CH:35]=1

Participants

Conditions

Temperature: 60 °C

Procedure

2-Aminoethanol (18 μL, 0.30 mmol) was added to a solution of ethanol (0.7 mL) containing (4Z)-4-(4-chlorobenzylidene)-2-{-4-[2-(4-methoxyphenyl)ethoxy]phenyl}-1,3-oxazol-5(4H)-one prepared in Example 1 (1c) (108 mg, 0.25 mmol). The mixture was stirred at 60° C. for 3 hours. The solvent was evaporated, and the residue was purified by thin layer chromatography for separation (ethyl acetate:methanol, 30:1, v/v, developed three times) to give 88 mg of the title compound (white amorphous solid, yield: 71%).

Workup

customThe solvent was evaporated
customthe residue was purified by thin layer chromatography for separation (ethyl acetate:methanol, 30:1, v/v, developed three times)

Sources & evidence

ORD record: ord-60c6d924d1d745c2a3ce50ccf94b9503
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497397B2

Reaction notes

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