Pyridine → HCID 21491666, compound

HRID 1973450Notes

Reaction equation

HRID 1973450 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][N:6]=[C:5]1[CH3:12].N1C=CC=CC=1.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>O>[CH3:19][S:20]([OH:22])(=[O:1])=[O:21].[OH:1][CH2:2][CH2:3][N:4]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][N:6]=[C:5]1[CH3:12]

Participants

5

Reactant 3

HCID 1049PyridineHCID 4173MetronidazoleHCID 31297Methanesulfonyl chloride

Product 1

HCID 21491666HCID 21491666, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

A suspension of 200 parts of 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole in 600 parts of pyridine is cooled to 5° C. in an ice bath and 140 parts of methanesulfonyl chloride is added portionwise at 0°-5° C. over a period of 4 hours. The mixture is then stirred at about 0° C. for 1 hour before it is slowly diluted with 600 parts of water while maintaining the temperature at 0°-5° C. The solid which forms is separated by filtration, washed with water and dried to give 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole methylsulfonate. Tosylates of 1-(2-hydroxyethyl)imidazoles are prepared in a similar manner using p-toluenesulfonyl chloride.

Workup

  1. temperaturewhile maintaining the temperature at 0°-5° C
  2. customThe solid which forms is separated by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-4ba8225a52fe431db36a183189ddaee9
Source dataset
uspto-grants-1976_12
Patent number
US03997572

Reaction notes

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