Methylamine → (E)-4-(2-(5-chlorothiophen-3-yl)-1-(4-(2-(methylamino)ethoxy)-phenyl)but-1-enyl)phenol

HRID 626108Notes

Reaction equation

HRID 626108 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8](/[C:11](/[C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=2)=[C:12](/[C:15]2[CH:19]=[C:18]([Cl:20])[S:17][CH:16]=2)\[CH2:13][CH3:14])=[CH:7][CH:6]=1.[CH3:28][NH2:29]>CO>[Cl:20][C:18]1[S:17][CH:16]=[C:15](/[C:12](/[CH2:13][CH3:14])=[C:11](\[C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=2)/[C:8]2[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][NH:29][CH3:28])=[CH:6][CH:7]=2)[CH:19]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 89672888(E)-4-(1-(4-(2-chloroethoxy)phenyl)-2-(5-chlorothiophen-3-yl)-but-1-enyl)phenol

Product 1

HCID 71617373(E)-4-(2-(5-chlorothiophen-3-yl)-1-(4-(2-(methylamino)ethoxy)-phenyl)but-1-enyl)phenolYield 35%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following the same procedure as described in example 11, step D, (E)-4-(1-(4-(2-chloroethoxy)phenyl)-2-(5-chlorothiophen-3-yl)but-1-enyl)phenol (0.8 g, 1.0 eq) was reacted with MeNH2 (30% wt in water, 10 mL) in MeOH (20 mL) at reflux to give 120 mg desired product (35% yield, E). 1H NMR (400 MHz, DMSO-d6) δ 9.30 (bs, 1H), 6.99-7.02 (m, 3H), 6.84-6.89 (m, 2H), 6.62-6.70 (m, 2H), 6.50-6.56 (m, 3H), 3.97 (t, J=5.6 Hz, 2H), 2.78 (t, J=5.6 Hz, 2H), 2.26-2.38 (m, 5H), 0.89 (t, J=7.2 Hz, 3H); m/z=414[M+1]+.

Workup

  1. temperatureat reflux

Sources & evidence

ORD record
ord-013772cfb46a4fe6a20790ee169ec08c
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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