Sodium Carbonate → 1-Methyl-2-(3-methyl-4-methylsulfinylphenyl-oxymethyl)-5-nitro-imidazole

HRID 441827Notes

Reaction equation

[CH3:1][N:2]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][N:4]=[C:3]1[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[C:14]([CH3:20])[CH:13]=1.ClC1C=CC=C(C(OO)=[O:29])C=1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl>[CH3:1][N:2]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][N:4]=[C:3]1[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH3:19])=[O:29])=[C:14]([CH3:20])[CH:13]=1

Participants

Conditions

Temperature: 25 °C

Procedure

29.3 g (0.1 mol) of 1-methyl-2-(3-methyl-4-methylthiophenyloxymethyl)-5-nitro-imidazole are dissolved in 200 ml of chloroform, and the solution is added dropwise while stirring at 25° C. to a solution of 17.25 g (0.1 mol) of 3-chloroperbenzoic acid in 70 ml of chloroform. The reaction mixture is stirred for 1 hour at 25° C., shaken with dilute sodium carbonate solution, the chloroform phase is separated, dried over sodium sulfate and concentrated by evaporation. The residue is recrystallized from ethanol with an addition of charcoal, to yield 21.0 g (68% of the theoretical yield) of 1-methyl-2-(3-methyl-4-methylsulfinylphenyl-oxymethyl)-5-nitro-imidazole in the form of yellow crystals, m.p. 121° C.

Workup

additionthe solution is added dropwise
customthe chloroform phase is separated
dry with materialdried over sodium sulfate
concentrationconcentrated by evaporation
customThe residue is recrystallized from ethanol with an addition of charcoal
customto yield 21.0 g (68% of the

Sources & evidence

ORD record: ord-7fde2ed7a35a44ce9ac5ab32394b76b0
Source dataset: uspto-grants-1977_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04042705

Reaction notes

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