Iodoacetamide → HCID 20475727, Verbindung

Reaktionsgleichung

Cl.[CH3:2][C:3]1[C:8]([Br:9])=[C:7]([CH3:10])[NH:6][C:5](=[S:11])[N:4]=1.[OH-].[K+].I[CH2:15][C:16]([NH2:18])=[O:17]>>[C:16]([CH2:15][S:11][C:5]1[N:6]=[C:7]([CH3:10])[C:8]([Br:9])=[C:3]([CH3:2])[N:4]=1)(=[O:17])[NH2:18]

Komponenten

Edukt 3

HCID 3727Iodoacetamide

HCID 14797Potassium Hydroxide

HCID 20475758HCID 20475758, Verbindung

Produkt 1

HCID 20475727HCID 20475727, VerbindungAusbeute 72 %

Versuchsvorschrift

4,6-Dimethyl-5-bromopyrimidine-2-thione HCl salt (5 mmol) was added to ethanolic (60 ml) KOH (11.4 mmol), the solution stirred for 10 min at room temperature, iodoacetamide (5.7 mmol) added, the stirring continued for 20 min at room temperature and for 100 min at 70° C. (pH 8). The warm reaction mixture was filtered, the filtrate evaporated, the residue extracted with chloroform (150 ml), the chloroform solution washed and the dried (MgSO4) solution evaporated to leave the sulfide; yield 72%, m.p. 175°-177° C. (iPrOH). 1H NMR (DMSO-d6): δ2.50 (Me), 3.80 (SCH2).