Methanethioamide → 2-Guanidino-4-(4-thiazolyl)thiazole dihydrobromide

HRID 280735

Reaktionsgleichung

Reaktionsgleichung von HRID 280735
[BrH:1].[Br:2][CH2:3][C:4]([C:6]1[N:7]=[C:8]([NH:11][C:12]([NH2:14])=[NH:13])[S:9][CH:10]=1)=O.[CH:15]([NH2:17])=[S:16]>CN(C)C=O>[BrH:2].[BrH:1].[NH:11]([C:8]1[S:9][CH:10]=[C:6]([C:4]2[N:17]=[CH:15][S:16][CH:3]=2)[N:7]=1)[C:12]([NH2:14])=[NH:13]

Komponenten

4

Edukt 2

HCID 3005587MethanethioamideHCID 178419719HCID 178419719, Verbindung

Produkt 1

HCID 1784192712-Guanidino-4-(4-thiazolyl)thiazole dihydrobromideAusbeute 86,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 1.8 g (5.2 mmol) of 2-bromo-1-(2-guanidino-4-thiazolyl)ethanone hydrobromide, 0.34 g (5.5 mmol) of thioformamide, and 10 ml of dimethylformamide was stirred at room temperature for 2 hours. The mixture was concentrated and the residue was triturated with acetonitrile. The resulting precipitate was collected by filtration, washed with acetonitrile, and dried to afford 1.74 g (85%) of 2-guanidino-4-(4-thiazolyl)thiazole dihydrobromide. Th:s was dissolved in 10 ml of water, and 1 ml of saturated sodium bicarbonate solution was added. The resulting precipitate was collected by filtration, washed well with water, then acetonitrile, then dried in vacuo to afford 1.17 g of 2-guanidino-4-(4-thiazoyl)thiazole as a white solid, mp 220°-222°; nmr (DMSO-d6) (δ): 8.96 (s, 1H); 7.96 (s, 1H); 7.18 (s, 1H); 7.0 (b, 4H); calcd. for C7H7N5S2 : C, 37.32; H, 3.13; N, 31.09; found: 36.94; H, 3.52; N, 29.74.

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. customthe residue was triturated with acetonitrile
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with acetonitrile
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-f508f44100a44422b6dd008b86fcffd9
Quelldatensatz
uspto-grants-1986_05
Patentnummer
US04590299

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