Metronidazole → My 40.20

HRID 1872912Notes

Reaction equation

HRID 1872912 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][CH2:8][OH:9])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][N:3]=1.[CH3:13][S:14](Cl)(=[O:16])=[O:15]>N1C=CC=CC=1>[CH3:13][S:14]([O:9][CH2:8][CH2:7][N:6]1[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][N:3]=[C:2]1[CH3:1])(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 4173MetronidazoleHCID 31297Methanesulfonyl chloride

Product 1

HCID 93141My 40.20Yield 87.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

Metronidazole (5.0 g, 29.2 mmol) was dissolved in pyridine (10 ml), and a pyridine solution (10 ml) of methanesulfonyl chloride (3.5 g, 30.7 mmol) was added dropwise to the solution. After the mixture was stirred at room temperature for 5 hours, the solvent was distilled off under reduced pressure, and the residue was washed with water-ethanol and dried to obtain 6.4 g of the title compound.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. washthe residue was washed with water-ethanol
  3. customdried

Sources & evidence

ORD record
ord-9ec146d9d4784dbd95530cabd85e2f32
Source dataset
uspto-grants-2000_08
Patent number
US06110967

Reaction notes

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