3-Chloro-4-(2-diethylaminoethoxy)phenylamine → 3-(2,4,6-trichlorophenyl)propynoic acid-[3-chloro-4-(2-diethylaminoethoxy)phenyl]amide Hydrochloride

HRID 735088Notes

Reaction equation

HRID 735088 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[C:10]#[C:11][C:12]([OH:14])=O.[Cl:15][C:16]1[CH:29]=[C:28]([NH2:30])[CH:27]=[CH:26][C:17]=1[O:18][CH2:19][CH2:20][N:21]([CH2:24][CH3:25])[CH2:22][CH3:23].ClCCl.CO.N>>[ClH:1].[Cl:15][C:16]1[CH:29]=[C:28]([NH:30][C:12](=[O:14])[C:11]#[C:10][C:3]2[C:4]([Cl:9])=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[CH:27]=[CH:26][C:17]=1[O:18][CH2:19][CH2:20][N:21]([CH2:24][CH3:25])[CH2:22][CH3:23]

Participants

4

Reactant 3

HCID 167916763-Chloro-4-(2-diethylaminoethoxy)phenylamineHCID 21584172Ammonia methanol dichloromethaneHCID 68816017(2,4,6-trichlorophenyl)propynoic Acid

Product 1

HCID 688192753-(2,4,6-trichlorophenyl)propynoic acid-[3-chloro-4-(2-diethylaminoethoxy)phenyl]amide Hydrochloride

Procedure

Prepared analogously to Example 2.3.f. from (2,4,6-trichlorophenyl)propynoic acid and [2-(2-chloro-4-aminophenoxy)ethyl]diethylamine. Yield: 0.72 g (82.9% of theory); melting point: 188° C.-191° C.; C21H20Cl4N2O2*HCl (M=510.67); calc.: molecular ion peak (M+H)+: 473/475/477/479/481; found: molecular ion peak (M+H)+: 473/475/477/479/481; Rf value: 0.4 (silica gel, dichloromethane/methanol/ammonia (90:10:0.1)).

Workup

  1. customPrepared analogously to Example 2.3.f

Sources & evidence

ORD record
ord-346d59803c284c358c7e42e58c94db68
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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