Hydrochloric Acid → 2-(2-Mercapto-2-methylpropylamino)-1-[2-(2-propynylthio)-2-methylpropylamino]benzene hydrochloride

HRID 1090051Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1090051
[ClH:1].[SH:2][C:3]([CH3:22])([CH3:21])[CH2:4][NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH:12][CH2:13][C:14]([S:17][CH2:18][C:19]#[CH:20])([CH3:16])[CH3:15]>C(OCC)C>[ClH:1].[SH:2][C:3]([CH3:22])([CH3:21])[CH2:4][NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH:12][CH2:13][C:14]([S:17][CH2:18][C:19]#[CH:20])([CH3:15])[CH3:16]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 195818T 691

Produkt 1

HCID 199142632-(2-Mercapto-2-methylpropylamino)-1-[2-(2-propynylthio)-2-methylpropylamino]benzene hydrochlorideAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

The HCl salt of each 2-(2-mercapto-2-methylpropylamino)-1-[2-(2-propynylthio)-2-methylpropyl-amino]benzene fraction was made by separately dissolving the free amine in 100 ml diethyl ether and cooling the mixture in an ice-H2O bath to 5° C. Anhydrous HCl gas was bubbled through the solution for 3 minutes, which resulted in the precipitation of an amorphous beige solid. The HCl gas and diethyl ether were removed by placing the solution in a 40° C. water bath, and passing a nitrogen stream over the solution. The first sample was recrystallized from ethanol and hexane to give 8.5 g (37% yield, 98.5% purity) of a crystalline, white solid. The second fraction required three successive recrystallizations to obtain a similar purity; 6 g (26% yield, 98% purity). A total of 14.5 g (65% yield) of 2-(2-mercapto-2-methylpropylamino)-1-[2-(2-propynylthio)-2-methylpropylamino]benzene hydrochloride was obtained.

Aufarbeitung

  1. customAnhydrous HCl gas was bubbled through the solution for 3 minutes
  2. customwhich resulted in the precipitation of an amorphous beige solid
  3. customThe HCl gas and diethyl ether were removed
  4. customin a 40° C.
  5. customThe first sample was recrystallized from ethanol and hexane
  6. customto give 8.5 g (37% yield, 98.5% purity) of a crystalline, white solid
  7. customthree successive recrystallizations
  8. customto obtain a similar purity; 6 g (26% yield, 98% purity)

Quellen und Nachweise

ORD-Eintrag
ord-7a60b4af9a904a33a4e78b86d100862f
Quelldatensatz
uspto-grants-1992_01
Patentnummer
US05080884

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