Hydrogen Sulfide → 3-[2-(Dimethylamino)ethyl]-1H-indole-5-carbothioamide

HRID 1762483

Reaktionsgleichung

Reaktionsgleichung von HRID 1762483
[CH3:1][N:2]([CH3:16])[CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]#[N:15])[CH:12]=2)[NH:7][CH:6]=1.C(N(CC)CC)C.[SH2:24]>CN(C)C=O>[CH3:16][N:2]([CH3:1])[CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14](=[S:24])[NH2:15])[CH:12]=2)[NH:7][CH:6]=1

Komponenten

5

Edukt 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 28511Indole-5-carbonitrile, 3-(2-dimethylaminoethyl)-

Produkt 1

HCID 200413563-[2-(Dimethylamino)ethyl]-1H-indole-5-carbothioamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 3-[2-(dimethylamino)ethyl]-1H-indole-5-carbonitrile (13.0 g) and triethylamine (50 ml) in dimethylformamide (300 ml) was stirred for 2 h whilst gaseous hydrogen sulphide was bubbled through it. More triethylamine (10 ml) was added and the solution was stirred at room temperature for 2 days, then evaporated in vacuo to give an oil (15 g) which was partitioned between ethyl acetate (500 ml) and water (3×250 ml). The organic layer was dried (MgSO4) pre-absorbed onto silica and purified by flash chromatography (A). The appropriate fractions were combined, concentrated in vacuo and triturated with ether (250 ml) to give the title compound (12.0 g) as a solid, m.p. 155°.

Aufarbeitung

  1. customwas bubbled through it
  2. additionMore triethylamine (10 ml) was added
  3. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2faf13d4fbc9489b9d679b30d03af470
Quelldatensatz
uspto-grants-1989_05
Patentnummer
US04833153

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