Hydrochloric Acid → (2R)-3-(2-Chloro-4-nitro-1H-imidazol-1-yl)-2-methyl-1,2-propanediol

HRID 856146Notes

Reaction equation

HRID 856146 reaction equation
[Cl:1][C:2]1[NH:3][CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[N+](C1C=CC(C([O:19][CH2:20][C:21]2([CH3:24])[CH2:23][O:22]2)=O)=CC=1)([O-])=O.C(N(CC)CC)C.Cl.S([O-])([O-])(=O)=O.[Mg+2]>C(OCC)(=O)C.C(=O)([O-])[O-].[K+].[K+]>[Cl:1][C:2]1[N:3]([CH2:23][C:21]([OH:22])([CH3:24])[CH2:20][OH:19])[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 3897930(2-Methyloxiran-2-yl)methyl 4-nitrobenzoateHCID 178526855HCID 178526855, compound

Product 1

HCID 23081081(2R)-3-(2-Chloro-4-nitro-1H-imidazol-1-yl)-2-methyl-1,2-propanediolYield 72.7%

Reagents, catalysts & solvents 2

HCID 11430Potassium CarbonateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-4-nitro-1H-imidazole (6.78 g, 46 mmol) and 2-methyloxiran-2-ylmethyl 4-nitrobenzoate (12 g, 51 mmol) were dissolved in ethyl acetate (24 ml), and triethylamine (1.3 ml, 9.2 mmol) was added to the solution. The resulting mixture was stirred under reflux for 14 hours. The reaction mixture was concentrated under reduced pressure, and methylene chloride (40 ml) was added to the residue. The resulting precipitates were filtered off, and dissolved in methanol (120 ml). To the solution, potassium carbonate (318 mg, 2.3 mmol) was added, and the resulting mixture was stirred at room temperature for 1 hour. To the resulting mixture, 6 N hydrochloric acid (0.8 ml) and magnesium sulfate (8 g) were added in this order with cooling on ice-bath, and the resulting mixture was stirred for 30 minutes. Insoluble matters were removed by filtration through Celite, and the filtrate was concentrated under reduced pressure. To the residue, ethyl acetate (6 ml) and toluene (60 ml) were added. The resulting precipitates were filtered off and dried at 50° C. to afford 2-chloro-1-(2,3-dihydroxy-2-methylpropyl)-4-nitroimidazole (7.88 g, yield 72%) as a white powder.

Workup

  1. temperatureunder reflux for 14 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and methylene chloride (40 ml)
  3. additionwas added to the residue
  4. customThe resulting precipitates
  5. filtrationwere filtered off
  6. dissolutiondissolved in methanol (120 ml)
  7. stirringthe resulting mixture was stirred at room temperature for 1 hour
  8. temperaturewith cooling on ice-bath
  9. stirringthe resulting mixture was stirred for 30 minutes
  10. customInsoluble matters were removed by filtration through Celite
  11. concentrationthe filtrate was concentrated under reduced pressure
  12. additionTo the residue, ethyl acetate (6 ml) and toluene (60 ml) were added
  13. customThe resulting precipitates
  14. filtrationwere filtered off
  15. customdried at 50° C.

Sources & evidence

ORD record
ord-323b1834235348d6ab42ac675a06f6fd
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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