Potassium Carbonate → 2-(((1-Methyl-5-nitroimidazol-2-yl)methyl)thio)pyridine

HRID 1287498Notes

Reaction equation

[CH3:1][N:2]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][N:4]=[C:3]1[CH2:10]OC(=O)C1C=CC=CC=1.[SH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[CH3:1][N:2]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][N:4]=[C:3]1[CH2:10][S:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1

Participants

Conditions

Temperature: 80 °C

Procedure

26.1 Grams (0.1 mol) of 1-methyl-2-benzoyloxymethyl-5-nitro-imidazole were dissolved while stirring in 150 ml of dimethylformamide; then 11.1 g (0.1 mol) of 2-mercaptopyridine and 13.8 g of potash (free from water and powdered) were added. A very faintly exothermic reaction was perceptible only. The reaction mixture was heated to 80°C for 1 hour, whereupon the color of the mixture changed from yellow toward light brown and a white precipitate formed. The mixture was then cooled to room temperature and the end product was precipitated by stirring it into about 500 ml of ice water. The product was suction-filtered, thoroughly washed with water and recrystallized from about 3000 ml of isopropanol. 18.0 Grams (72 % of the theoretical yield) of 1-methyl-2-(2-pyridylthiomethyl)-5-nitro-imidazole were obtained as a faintly yellow crystallized powder, m.p. 146°-147°C.

Workup

customA very faintly exothermic reaction
customformed
temperatureThe mixture was then cooled to room temperature
customthe end product was precipitated
filtrationThe product was suction-filtered
washthoroughly washed with water
customrecrystallized from about 3000 ml of isopropanol

Sources & evidence

ORD record: ord-a3518f19ef704547925d366589a08d2d
Source dataset: uspto-grants-1976_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03984560

Reaction notes

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