1-(2-Bromoethyl)-2-methyl-5-nitroimidazole → Tinidazole

HRID 971469Notes

Reaction equation

HRID 971469 reaction equation
Br[CH2:2][CH2:3][N:4]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][N:6]=[C:5]1[CH3:12].[Na].[CH2:14]([S:16]([OH:18])=[O:17])[CH3:15]>CS(C)=O>[CH2:14]([S:16]([CH2:2][CH2:3][N:4]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][N:6]=[C:5]1[CH3:12])(=[O:18])=[O:17])[CH3:15]

Participants

5

Reactant 3

HCID 801631-(2-Bromoethyl)-2-methyl-5-nitroimidazoleHCID 435496Ethanesulfinic acidHCID 5360545Sodium

Product 1

HCID 5479Tinidazole

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

5.83 g. (25 m moles) of 1-(2'-bromoethyl)-2-methyl-5-nitroimidazole is dissolved in 50 ml. of dimethylsulfoxide and 5.48 g. (30 m mole) of the sodium salt of ethyl sulfinic acid (CH3CH2SO2Na) is added. The reaction mixture is maintained for 21/2 hours at 100°-110° C. thereafter the solvent is removed under vacuum and the solid residue is washed with water and recrystallized from ethanol. The yield is 2.28 (37%) of 1-[2'-(ethylsulfonyl)-ethyl]-2-methyl-5-nitroimidazole, M.P. 124°-126° C.

Workup

  1. temperatureThe reaction mixture is maintained for 21/2 hours at 100°-110° C.
  2. customthe solvent is removed under vacuum
  3. washthe solid residue is washed with water
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-7acfe97b781245468d9dddf48f2cda21
Source dataset
uspto-grants-1979_07
Patent number
US04160096

Reaction notes

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