Hydrogen Sulfide → HCID 178505162, Verbindung

HRID 364307Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 364307
[CH3:1][S:2]([NH:5][C:6]([NH:8][CH2:9][C:10]([F:13])([F:12])[F:11])=S)(=[O:4])=[O:3].[F:14][C:15]([F:32])([F:31])[CH2:16][N:17]=[C:18]([NH2:30])[NH:19][C:20]1[S:21][CH:22]=[C:23]([CH2:25]CCCN)[N:24]=1.[SH2:33].C(Cl)(Cl)Cl.[CH3:38]O.N.C[N:42]([CH3:45])C=O>[N+]([O-])([O-])=O.[Ag+]>[F:32][C:15]([F:14])([F:31])[CH2:16][N:17]=[C:18]([NH2:30])[NH:19][C:20]1[S:21][CH:22]=[C:23]([CH2:25][S:33][CH2:38][CH2:45][NH:42][C:6]([NH:8][CH2:9][C:10]([F:13])([F:12])[F:11])=[N:5][S:2]([CH3:1])(=[O:4])=[O:3])[N:24]=1

Komponenten

7

Edukt 5

HCID 402Hydrogen SulfideHCID 6228Dimethylformamide2×HCID 212987102-[2-(2,2,2-Trifluoroethyl)-guanidino]-4-(4-aminobutyl)thiazoleHCID 212988431-Methanesulphonyl-3-(2,2,2-trifluoroethyl)thioureaHCID 21866414Chloroform methanol ammonia

Produkt 1

HCID 178505162HCID 178505162, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24470Silver NitrateKatalysator

Versuchsvorschrift

To a solution containing 1-methanesulphonyl-3-(2,2,2-trifluoroethyl)thiourea (0.09 g.) and 2-[2-(2,2,2-trifluoroethyl)guanidino]-4-(4-aminobutyl)thiazole (0.13 g.) in dimethylformamide (4 ml.) was added a solution of silver nitrate (0.14 g.) in dimethylformamide (2 ml.). After allowing it to stand at room temperature for 3 hours the reaction mixture was treated with an excess of gaseous hydrogen sulphide and the precipitated silver sulphite filtered off. The residue obtained on evaporation of the filtrate was subjected to preparative thin layer chromatography using chloroform/methanol/ammonia 90:10:0.1 v/v/v for development. Isolation of the appropriate zone of the chromatogram and extraction with hot ethanol/chloroform 50:50 v/v (150 ml.) gave a yellow residue which on crystallisation from methanol afforded 2-[2-(2,2,2-trifluoroethyl)guanidino]-4-[2-(2-methylsulphonyl-3-[2,2,2-trifluoroethyl]guanidino)ethylthiomethyl]thiazole which contained one mole of methanol of crystallisation. The n.m.r. spectrum in d6 l dimethylsulphoxide containing a little d4 acetic acid and using tetramethylsilane as internal standard (δ=0) included the following resonances (δ):2.8 (3H, singlet); 4.0 (2H, multiplet); 4.1 (2H, multiplet); 6.4 (1H, singlet).

Aufarbeitung

  1. filtrationthe precipitated silver sulphite filtered off
  2. customThe residue obtained on evaporation of the filtrate
  3. extractionIsolation of the appropriate zone of the chromatogram and extraction with hot ethanol/chloroform 50:50 v/v (150 ml.)
  4. customgave a yellow residue which
  5. customon crystallisation from methanol

Quellen und Nachweise

ORD-Eintrag
ord-9a7137aeb3bd4cc0960543943c732048
Quelldatensatz
uspto-grants-1986_08
Patentnummer
US04604465

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