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

HRID 735079Notes

Reaction equation

HRID 735079 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].[Cl:14][C:15]1[CH:28]=[C:27]([NH2:29])[CH:26]=[CH:25][C:16]=1[O:17][CH2:18][CH2:19][N:20]([CH2:23][CH3:24])[CH2:21][CH3:22]>C1(C)C=CC=CC=1>[Cl:14][C:15]1[CH:28]=[C:27]([NH:29][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:26]=[CH:25][C:16]=1[O:17][CH2:18][CH2:19][N:20]([CH2:23][CH3:24])[CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 167916763-Chloro-4-(2-diethylaminoethoxy)phenylamineHCID 87587808(2,4-dichlorophenyl)propynoic Acid Chloride

Product 1

HCID 578457513-(2,4-Dichlorophenyl)propynoic acid-[3-chloro-4-(2-diethylaminoethoxy)phenyl]amide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

0.37 g (1.58 mmol) of (2,4-dichlorophenyl)propynoic acid chloride is dissolved in 15 mL of absolute toluene and while cooling with ice combined with 0.77 g (3.16 mmol) of [2-(2-chloro-4-aminophenoxy)ethyl]diethylamine, dissolved in 10 mL of absolute toluene, and stirred for 4 hours at ambient temperature. Then the reaction mixture is extracted with ethyl acetate and dilute aqueous ammonia solution. The organic phase is extracted with water and dried over sodium sulfate. The purification is carried out by column chromatography on silica gel (eluant: dichloromethane/methanol (9:1)). The product obtained is recrystallized from petroleum ether and dried in the vacuum drying chamber at 50° C. Yield: 0.21 g (30.2% of theory); melting point: 98° C.-100° C.; C21H21Cl3N2O2 (M=439.77); calc.: molecular ion peak (M+H)+: 439/441/443; found: molecular ion peak (M+H)+: 439/441/443; Rf value: 0.5 (silica gel, dichloromethane/methanol/ammonia (9:1:0.1)).

Workup

  1. temperaturewhile cooling with ice
  2. extractionThen the reaction mixture is extracted with ethyl acetate and dilute aqueous ammonia solution
  3. extractionThe organic phase is extracted with water
  4. dry with materialdried over sodium sulfate
  5. customThe purification
  6. customThe product obtained
  7. customis recrystallized from petroleum ether
  8. customdried in the vacuum
  9. customdrying chamber at 50° C

Sources & evidence

ORD record
ord-96a360af9918488e9b65df1573ad625e
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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