Propiolic Acid → 3-[(1H-Indol-3-yl)sulfanyl]prop-2-enoic acid

HRID 918473Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 918473
[C:1]([OH:5])(=[O:4])[C:2]#[CH:3].[SH:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1>[OH-].[Na+]>[NH:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7]([S:6][CH:3]=[CH:2][C:1]([OH:5])=[O:4])=[CH:8]1

Komponenten

4

Edukt 2

HCID 10110Propiolic AcidHCID 102001H-Indole-3-thiol

Produkt 1

HCID 544439283-[(1H-Indol-3-yl)sulfanyl]prop-2-enoic acidAusbeute 80,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14798Sodium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

A mixture of 35.0 g (0.5 mole) of propiolic acid, 97 g (0.5 mole) of 3-mercaptoindole and 500 ml of 1N NaOH solution is stirred for 1 hour at 95°C. The solution is cooled and the precipitated solid washed with water and discarded. The filtrate is acidified with 4N HCl and the gummy precipitate extracted with ether. The ether is dried and evaporated and the residue recrystallized from 250 ml of acetonitrile to give 88 g of product, mp 172-173°C.

Aufarbeitung

  1. temperatureThe solution is cooled
  2. washthe precipitated solid washed with water
  3. extractionthe gummy precipitate extracted with ether
  4. dry with materialThe ether is dried
  5. customevaporated
  6. customthe residue recrystallized from 250 ml of acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-df35bca2828446d5b51ebe6ab69b41b1
Quelldatensatz
uspto-grants-1976_07
Patentnummer
US03971806

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