Sulfuric Acid → Fexinidazole

HRID 441828Notes

Reaction equation

HRID 441828 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][C:19]#N)=[CH:14][CH:13]=1.S(=O)(=O)(O)O.COS(OC)(=O)=O>>[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])=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 6497Dimethyl SulfateHCID 21418419HCID 21418419, compound

Product 1

HCID 68792Fexinidazole

Conditions

Temperature
60 °C

Procedure

5.8 g (0.02 mols) of 1-methyl-2-(4-thiocyanatophenyloxymethyl)-5-nitro-imidazole are introduced portionwise while stirring, under a nitrogen atmosphere, at room temperature, into a mixture of 26.5 ml of concentrated sulfuric acid and 5.0 g (0.04 mol) of dimethylsulfate and allowed to stand overnight at room temperature. The solution is then heated to 60° C. for 30 minutes, cooled and poured onto ice/water. The precipiate is suction-filtered and washed with water. In addition to bis-4,4'-(1-methyl-5-nitro-imidazolyl-2-methoxy)-diphenyl disulfide (m.p. 160° C.), column chromatographical purification on silica gel yields the 1-methyl-2-(4-methylthiophenyl-oxymethyl)-5-nitro-imidazole, m.p. 116° C.

Workup

  1. temperaturecooled
  2. additionpoured onto ice/water
  3. filtrationThe precipiate is suction-filtered
  4. washwashed with water
  5. additionIn addition
  6. customto bis-4,4'-(1-methyl-5-nitro-imidazolyl-2-methoxy)-diphenyl disulfide (m.p. 160° C.), column chromatographical purification on silica gel

Sources & evidence

ORD record
ord-907cc200f7bb42aa8cfcd6c29c35a7c3
Source dataset
uspto-grants-1977_08
Patent number
US04042705

Reaction notes

Loading…