Bis(2-aminophenyl) disulfide → HCID 23049817, Verbindung

HRID 1651507

Reaktionsgleichung

Reaktionsgleichung von HRID 1651507
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][S:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH2:16].Br[C:18]([CH3:23])([CH3:22])[C:19](Cl)=[O:20]>C(#N)C>[O:20]=[C:19]1[C:18]([CH3:23])([CH3:22])[C:12]2[C:11](=[C:10]([S:9][S:8][C:3]3[CH:4]=[CH:5][CH:6]=[C:7]4[C:2]=3[NH:1][C:19](=[O:20])[C:18]4([CH3:23])[CH3:22])[CH:15]=[CH:14][CH:13]=2)[NH:16]1

Komponenten

4

Edukt 2

HCID 14358Bis(2-aminophenyl) disulfideHCID 111060492-Bromo-2-methylpropanoyl chloride

Produkt 1

HCID 23049817HCID 23049817, VerbindungAusbeute 55,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

In a stream of nitrogen, 12.4 g of bis(2-aminophenyl)disulfide was added to 100 ml of acetonitrile, and further added thereto was 18.6 g of α-bromo-α-methylpropionic acid chloride. The resulting mixture was heated under reflux for 3 hours. After removal of acetonitrile, 100 ml of ethylene chloride was added to the reaction product, and gradually added thereto was 28 g of anhydrous aluminium chloride at room temperature. After the conclusion of the additional materials, the mixture was heated for 2 hours at 40° C. with vigorous stirring. The reaction mixture was poured into 200 g of ice-cold water containing concentrated hydrochloric acid in order to decompose the aluminium chloride. After the decomposition, 100 ml of chloroform was added to the reaction mixture, and the organic phase was washed with saturated sodium chloride solution three times. The chloroform-ethylene chloride phase was removed, and concentrated to dryness. The product was purified by column chromatography on silica gel to obtain 10.6 g of bis(2-oxo-3,3-di-methyl-7-indolinyl)disulfide.

Aufarbeitung

  1. additionfurther added
  2. temperatureThe resulting mixture was heated
  3. temperatureunder reflux for 3 hours
  4. customAfter removal of acetonitrile, 100 ml of ethylene chloride
  5. additionwas added to the reaction product
  6. additiongradually added
  7. customat room temperature
  8. additionThe reaction mixture was poured into 200 g of ice-cold water containing concentrated hydrochloric acid in order
  9. additionAfter the decomposition, 100 ml of chloroform was added to the reaction mixture
  10. washthe organic phase was washed with saturated sodium chloride solution three times
  11. customThe chloroform-ethylene chloride phase was removed
  12. concentrationconcentrated to dryness
  13. customThe product was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-fb615c9d032245cc9e2fad740f843619
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04929540

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