Ammonia methanol dichloromethane → 3-(2,4-dichlorophenyl)propynoic acid-[3-methoxy-4-(2-diethylaminoethoxy)phenyl]amide Hydrochloride

HRID 735090Notes

Reaction equation

HRID 735090 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]#[C:10][C:11](Cl)=[O:12].[CH3:14][O: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].[CH3:14][O:15][C:16]1[CH:29]=[C:28]([NH:30][C:11](=[O:12])[C:10]#[C:9][C:3]2[CH:4]=[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 21584172Ammonia methanol dichloromethaneHCID 224961344-(2-Diethylaminoethoxy)-3-methoxyphenylamineHCID 87587808(2,4-dichlorophenyl)propynoic Acid Chloride

Product 1

HCID 688192023-(2,4-dichlorophenyl)propynoic acid-[3-methoxy-4-(2-diethylaminoethoxy)phenyl]amide Hydrochloride

Procedure

Prepared analogously to Example 2.3.f. from (2,4-dichlorophenyl)propynoic acid chloride and [2-(2-methoxy-4-aminophenoxy)ethyl]diethylamine. Yield: 0.25 g (31.2% of theory); melting point: 205° C.-207° C.; C22H24Cl2N2O3*HCl (M=471.81); calc.: molecular ion peak (M+H)+: 435/437/439; found: molecular ion peak (M+H)+: 435/437/439; Rf value: 0.6 (silica gel, dichloromethane/methanol/ammonia (50:10:0.1)).

Workup

  1. customPrepared analogously to Example 2.3.f

Sources & evidence

ORD record
ord-0fa7e9cee5274d399cf7a2ecf6a16e81
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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