HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Hydrochloric Acid → (betaR)-2-Chloro-beta-hydroxy-beta-methyl-4-nitro-1H-imidazole-1-propanol1-Methanesulfonate

HRID 856147
Notes
Print preview

Reaction equation

HRID 856147 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Cl:6][C:7]1[N:8]([CH2:15][C:16]([OH:20])([CH3:19])[CH2:17][OH:18])[CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[N:11]=1.Cl>N1C=CC=CC=1>[Cl:6][C:7]1[N:8]([CH2:15][C:16]([OH:20])([CH3:19])[CH2:17][O:18][S:2]([CH3:1])(=[O:4])=[O:3])[CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[N:11]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 23081081(2R)-3-(2-Chloro-4-nitro-1H-imidazol-1-yl)-2-methyl-1,2-propanediol

Product 1

HCID 23081345(betaR)-2-Chloro-beta-hydroxy-beta-methyl-4-nitro-1H-imidazole-1-propanol1-MethanesulfonateYield 100%

Reagents, catalysts & solvents 1

HCID 1049
Pyridine
Solvent

Procedure

Methanesulfonyl chloride (2.01 ml, 25.72 mmol) was added to a solution of 2-chloro-1-(2,3-dihydroxy-2-methylpropyl)-4-nitroimidazole prepared in Example 3 (5.05 g, 21.43 mmol) in pyridine (10 ml) with cooling on ice-bath and the resulting mixture was stirred at room temperature for 1.5 hours. 6N hydrochloric acid was added to the mixture, and the resulting mixture was extracted with ethyl acetate. The organic phase was dried over magnesium sulfate, and then concentrated under reduced pressure to afford 2-chloro-1-(2-hydroxy-3-methanesulfonyloxy-2-methylpropyl)-4-nitroimidazole (6.72 g, quantitative) as a yellow oil.

Workup

  1. temperaturewith cooling on ice-bath
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-190057c901004ad58aec48ac72fce09e
Source dataset
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07262212B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes