Ethylamine → 4-(2-(2-Chlorobenzofuran-5-yl)-1-(4-(2-(ethylamino)ethoxy)phenyl)but-1-enyl)phenol

HRID 626264Notes

Reaction equation

HRID 626264 reaction equation
[Cl:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([C:11]([CH2:30][CH3:31])=[C:12]([C:23]3[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=3)[C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21]Cl)=[CH:15][CH:14]=3)=[CH:7][C:5]=2[CH:6]=1.[CH2:32]([NH2:34])[CH3:33]>CO>[Cl:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([C:11]([CH2:30][CH3:31])=[C:12]([C:23]3[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=3)[C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][NH:34][CH2:32][CH3:33])=[CH:15][CH:14]=3)=[CH:7][C:5]=2[CH:6]=1

Participants

4

Reactant 2

HCID 6341EthylamineHCID 1239950204-(2-(2-Chlorobenzofuran-5-yl)-1-(4-(2-chloroethoxy)phenyl)but-1-enyl)phenol

Product 1

HCID 726804784-(2-(2-Chlorobenzofuran-5-yl)-1-(4-(2-(ethylamino)ethoxy)phenyl)but-1-enyl)phenolYield 54%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

According to the same procedure as example 1, step E described, 4-(2-(2-chlorobenzofuran-5-yl)-1-(4-(2-chloroethoxy)phenyl)but-1-enyl)phenol (70 mg, 1.0 eq, made by example 11, step D) was reacted with ethanamine (3 mL) in MeOH (8 mL) under reflux to give the desired product (38 mg, 54%, Z/E=1/1.2) as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.23 (s, 1H), 7.20 (d, J=8.4 Hz, 1H), 7.12 & 7.03 (d, J=8.6 Hz, 2H), 6.99 (d, J=8.8 Hz, 1H), 6.83 & 6.75 (d, J=8.8 Hz, 2H), 6.71 & 6.65 (d, J=8.6 Hz, 2H), 6.44 (s, 1H), 6.45 & 6.40 (d, J=8.4 Hz, 2H), 4.10 & 3.92 (t, J=4.8 Hz, 2H), 3.04 & 2.93 (t, J=4.8 Hz, 2H), 2.78 & 2.71 (q, J=7.2 Hz, 2H), 2.50 (q, J=7.2 Hz, 2H), 1.18 & 1.13 (q, J=7.2 Hz, 3H), 0.91 (t, J=7.2 Hz, 3H); m/z=462[M+1]+.

Workup

  1. temperatureunder reflux

Sources & evidence

ORD record
ord-6711cd58c2de4a5f983e3be55b1d6d0e
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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