Triethylamine → 4-[(4-prop-1-ynylphenylcarbamoyl)ethynyl]benzyl Methanesulfonate

HRID 734994Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 734994
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:27])[C:17]#[C:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][OH:26])=[CH:21][CH:20]=2)=[CH:11][CH:10]=1)#[C:7][CH3:8].C(N(CC)CC)C>ClCCl>[CH3:1][S:2]([O:26][CH2:25][C:22]1[CH:21]=[CH:20][C:19]([C:18]#[C:17][C:16](=[O:27])[NH:15][C:12]2[CH:11]=[CH:10][C:9]([C:6]#[C:7][CH3:8])=[CH:14][CH:13]=2)=[CH:24][CH:23]=1)(=[O:4])=[O:3]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 688177323-(4-Hydroxymethylphenyl)propynoic acid (4-prop-1-ynylphenyl)amide

Produkt 1

HCID 866018854-[(4-prop-1-ynylphenylcarbamoyl)ethynyl]benzyl Methanesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

0.14 mL (1.8 mmol) of methanesulfonic acid chloride is slowly added dropwise at ambient temperature to a solution of 0.5 g (1.72 mmol) of 3-(4-hydroxymethylphenyl)propynoic acid (4-prop-1-ynylphenyl)amide and 0.49 mL (3.6 mmol) of triethylamine in 20 mL of dichloromethane and the reaction mixture is stirred for 2 hours at ambient temperature. It is extracted three times with water and the organic phase is dried over sodium sulfate. The solvent is distilled off and the residue is stirred with diisopropyl ether. Yield: 0.48 g (75.6% of theory); C20H17NO4S (M=367.42); calc.: molecular ion peak (M+H)+: 368; found: molecular ion peak (M+H)+: 368; Rf value: 0.48 (silica gel, dichloromethane/ethanol (20:1)).

Aufarbeitung

  1. extractionIt is extracted three times with water
  2. dry with materialthe organic phase is dried over sodium sulfate
  3. distillationThe solvent is distilled off
  4. stirringthe residue is stirred with diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-4823602759d3436084441dec45c9c3b3
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592373B2

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