Potassium Carbonate → 1-Methyl-2-(3-methyl-4-methylthiophenyloxymethyl)-5-nitro-imidazole

HRID 441825

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([OH:10])[CH:5]=[CH:6][C:7]=1[S:8][CH3:9].C(=O)([O-])[O-].[K+].[K+].[CH3:17][N:18]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][N:20]=[C:19]1[CH2:26]Cl>CN(C)C=O>[CH3:17][N:18]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][N:20]=[C:19]1[CH2:26][O:10][C:4]1[CH:5]=[CH:6][C:7]([S:8][CH3:9])=[C:2]([CH3:1])[CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 15.4 g (0.1 mol) of 3-methyl-4-methylmercaptophenol in 30 ml of dimethylformamide, 13.8 g (0.1 mol) of potassium carbonate powder are added, and then a solution of 17.6 g (0.1 mol) of 1-methyl-2-chloromethyl-5-nitro-imidazole in 40 ml of dimethylformamide is added dropwise while stirring at 25° C. The temperature of the faintly exothermal reaction is adjusted to at most 35° C. by cooling with ice water. The mixture is then stirred for another hour at 25° C., poured onto ice/water, the precipitate is suction-filtered, washed with water and recrystallized from methanol with an addition of charcoal to yield 21.7 g (74% of the theoretical yield) of 1-methyl-2-(3-methyl-4-methylthiophenyl-oxymethyl)-5-nitro-imidazole in the form of yellow crystals, m.p. 108° C.

Workup

customThe temperature of the faintly exothermal reaction
customis adjusted to at most 35° C.
stirringThe mixture is then stirred for another hour at 25° C.
additionpoured onto ice/water
filtrationthe precipitate is suction-filtered
washwashed with water
customrecrystallized from methanol with an addition of charcoal
customto yield 21.7 g (74% of the

Sources & evidence

ORD record: ord-7a0a46fecb9046b0b4951a4a38cda529
Source dataset: uspto-grants-1977_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04042705

Linked notes

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