3-(2,4-dichlorophenyl)prop-2-ynoic acid → 3-(2,4-Dichlorophenyl)propynoic acid-[4-(2-diethylaminopropoxy)phenyl]amide

HRID 735038Notes

Reaction equation

HRID 735038 reaction equation
[CH2:1]([N:3]([CH2:15][CH3:16])[CH:4]([CH3:14])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=1)[CH3:2].[Cl:17][C:18]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=1[C:25]#[C:26][C:27](O)=[O:28].ClCCl.C(O)C.N>>[CH2:15]([N:3]([CH2:1][CH3:2])[CH:4]([CH3:14])[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([NH:13][C:27](=[O:28])[C:26]#[C:25][C:19]2[CH:20]=[CH:21][C:22]([Cl:24])=[CH:23][C:18]=2[Cl:17])=[CH:11][CH:12]=1)[CH3:16]

Participants

4

Reactant 3

HCID 2285093-(2,4-dichlorophenyl)prop-2-ynoic acidHCID 22609213HCID 22609213, compoundHCID 688160894-(2-Diethylaminopropoxy)phenylamine

Product 1

HCID 688166003-(2,4-Dichlorophenyl)propynoic acid-[4-(2-diethylaminopropoxy)phenyl]amide

Procedure

Prepared analogously to Example 3.4.c. from 4-(2-diethylaminopropoxy)phenylamine and (2,4-dichlorophenyl)propynoic acid. Yield: 0.41 g (65.2% of theory); melting point: 70° C.-72° C.; C22H24Cl2N2O2 (M=419.35); calc.: molecular ion peak (M+H)+: 419/421/423; found: molecular ion peak (M+H)+: 419/421/423; Rf value: 0.4 (silica gel, dichloromethane/ethanol/ammonia (5:1:0.01)).

Workup

  1. customPrepared analogously to Example 3.4.c

Sources & evidence

ORD record
ord-faf5335c5c234af2af179a8d830c383f
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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