(2,4-Dichlorophenoxy)acetyl chloride → 2-(2,4-Dichloro-phenoxy)-n-[4-(2-diethylamino-ethoxy)-3-methoxy-phenyl]-acetamide

HRID 898557

Reaction equation

HRID 898557 reaction equation
[Cl:1][C:2]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6](Cl)=[O:7].[CH2:14]([N:16]([CH2:29][CH3:30])[CH2:17][CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][C:21]=1[O:27][CH3:28])[CH3:15].C(N(C(C)C)C(C)C)C>ClCCl>[Cl:1][C:2]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([NH:26][C:23]1[CH:24]=[CH:25][C:20]([O:19][CH2:18][CH2:17][N:16]([CH2:29][CH3:30])[CH2:14][CH3:15])=[C:21]([O:27][CH3:28])[CH:22]=1)=[O:7]

Participants

5

Reactant 3

HCID 69887(2,4-Dichlorophenoxy)acetyl chlorideHCID 81531DiisopropylethylamineHCID 224961344-(2-Diethylaminoethoxy)-3-methoxyphenylamine

Product 1

HCID 129974422-(2,4-Dichloro-phenoxy)-n-[4-(2-diethylamino-ethoxy)-3-methoxy-phenyl]-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 70 mg (0.290 mmol) of (2,4-dichloro-phenoxy)-acetylchloride in 0.5 mL dichloromethane was added to a solution of 66 mg (0.278 mmol) of 4-(2-diethylamino-ethoxy)-3-methoxy-phenylamine (intermediate product Z6b) and 96 μL (0.56 mmol) of ethyl-diisopropylamine in 1.5 mL abs. dichloromethane and the mixture was stirred for 15 hours at RT. The reaction mixture was evaporated down i. vac. and the residue was purified by column chromatography (silica gel, dichloromethane/MeOH 9:1).

Workup

  1. customThe reaction mixture was evaporated down i
  2. customand the residue was purified by column chromatography (silica gel, dichloromethane/MeOH 9:1)

Sources & evidence

ORD record
ord-5c6dc6a4ad93421fae363aea205c7220
Source dataset
uspto-grants-2008_04
Patent number
US07351719B2

Linked notes

Loading…