Dichloromethane → HCID 15714015, Verbindung

HRID 1709267Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1709267
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH:12]([CH3:25])[CH2:13][C:14]2[CH:24]=[CH:23][C:17]([O:18][CH2:19][C:20](O)=[O:21])=[CH:16][CH:15]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(Cl)[Cl:27]>O1CCCC1.S(Cl)(Cl)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH:12]([CH3:25])[CH2:13][C:14]2[CH:24]=[CH:23][C:17]([O:18][CH2:19][C:20]([Cl:27])=[O:21])=[CH:16][CH:15]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 6344DichloromethaneHCID 14579384(4-{2-[(4-Chlorobenzene-1-sulfonyl)amino]propyl}phenoxy)acetic acid

Produkt 1

HCID 15714015HCID 15714015, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

1.15 g 4-[2-(4-chlorophenyl)sulfonylaminopropyl]phenoxyacetic acid are dissolved in a mixture of 7 ml of methylene chloride and 7 ml of tetrahydrofuran, and 2.2 ml of thionyl chloride are added thereto. After the mixture is refluxed for 2 hours, the solvent is distilled off to give 4-[2-(4-chlorophenyl)sulfonylaminopropyl]phenoxyacetyl chloride as ocherous oil. The product obtained above is dissolved in 10 ml of tetrahydrofuran. The solution and 6 ml of 0.6N an aqueous sodium hydroxide solution are added dropwise to a mixture of 787 mg of 6-aminohexanoic acid, 11 ml of 0.6N an aqueous sodium hydroxide solution, 20 ml of ethanol and 10 ml of ether under stirring at the same time. After the mixture is stirred at room temperature overnight, 50 ml of water and 50 ml of ether are added thereto. The aqueous layer is made acidic with 10% hydrochloric acid, extracted with ethyl acetate, washed, dried, filtered, and evaporated to remove the solvent. Thus obtained pale yellow caramel is purified by silica gel column chromatography (solvent; chloroform, then chloroform: methanol=9:1) to give 1.50 g of 6-{ 4-[2-(4-chlorophenyl)sulfonylaminopropyl]phenoxyacetylamino}-n-hexanoic acid as colorless oil.

Aufarbeitung

  1. additionare added
  2. temperatureAfter the mixture is refluxed for 2 hours
  3. distillationthe solvent is distilled off

Quellen und Nachweise

ORD-Eintrag
ord-7ee3d2bf10444a56a415348b22a9257a
Quelldatensatz
uspto-grants-1990_08
Patentnummer
US04948810

Notizen zur Reaktion

Wird geladen…