Acetic Anhydride → HCID 178485063, Verbindung

Reaktionsgleichung

C(O[C:5](=[O:7])[CH3:6])(=O)C.[NH:8]([C:12]1[S:13][CH:14]=[C:15]([CH2:17][S:18][CH2:19][CH2:20][NH:21][C:22]([NH:26][CH3:27])=[N:23][C:24]#[N:25])[N:16]=1)[C:9]([NH2:11])=[NH:10]>N1C=CC=CC=1.O>[C:5]([N:10]=[C:9]([NH2:11])[NH:8][C:12]1[S:13][CH:14]=[C:15]([CH2:17][S:18][CH2:19][CH2:20][NH:21][C:22]([NH:26][CH3:27])=[N:23][C:24]#[N:25])[N:16]=1)(=[O:7])[CH3:6]

Komponenten

Versuchsvorschrift

Acetic anhydride (0.39 g.) was added to a stirred suspension of 2-guanidino-4-[2-(2-cyano-3-methylguanidino)ethylthiomethyl]thiazole (1.10 g.) in pyridine (6 ml.) at room temperature. After stirring for two hours, the mixture was diluted with water (50 ml.), extracted with methylene chloride (3×30 ml.) and the combined extracts washed with water (100 ml.) and dried over magnesium sulphate. The solution was filtered and evaporated to dryness to leave a gum which was purified by column chromatography (silica column, eluted with ethyl acetate/ethanol/ammonia (s.g. 0.880) 6:1:1 v/v/v to give 2-(2-acetylguanidino)-4-[2-(2-cyano-3-methylguanidino)ethylthiomethyl]thiazole as an amorphous solid. The n.m.r. spectrum in d6 dimethyl sulphoxide using tetramethylsilane as internal standard had the following resonances (δ): 2.1 (3H, singlet); 2.7 (5H, multiplet); 3.3 (multiplet, obscured by H2O); 3.7 (2H, singlet); 6.8 (1H, singlet); 7.0 (2H, broad multiplet); 9.0 (2H, very broad) and 10.7 (1H, broad).