Dimethylformamide → 2,5-Dibromo-1-methoxymethyl-4-nitroimidazole

HRID 1092860Notes

Reaction equation

HRID 1092860 reaction equation
[H-].[Na+].CN(C)C=O.[Br:8][C:9]1[NH:10][C:11]([Br:17])=[C:12]([N+:14]([O-:16])=[O:15])[N:13]=1.Cl[CH2:19][O:20][CH3:21]>O>[Br:8][C:9]1[N:10]([CH2:19][O:20][CH3:21])[C:11]([Br:17])=[C:12]([N+:14]([O-:16])=[O:15])[N:13]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7864Chloromethyl Methyl Ether2×HCID 24758Sodium hydride2×HCID 178526891HCID 178526891, compound

Product 1

HCID 5422602,5-Dibromo-1-methoxymethyl-4-nitroimidazoleYield 84.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under an ice-cooling condition, sodium hydride (3.56 g) was added to a N,N-dimethylformamide (100 ml) solution of 2,5-dibromo-4-nitroimidazole (20.08 g). 10 minutes later, being added dropwise chloromethylmethyl ether (6.75 ml) thereto at 10 to 15° C., then the reaction mixture was turned back to a room temperature. After being stirred this reaction mixture for 5 hours, under an ice-cooling condition, sodium hydride (0.30 g) and chloromethylmethyl ether (0.56 ml) were added, further stirred at a room temperature for 1 hour. Then the reaction mixture was ice-cooled, water was added and extracted with ethyl acetate. The organic layer was washed with an aqueous solution being saturated with sodium chloride, dried over anhydrous sodium sulfate, then concentrated under a reduced pressure. Thus obtained crude crystals were washed with diisopropyl ether, and dried at 50° C. for 24 hours, there was obtained 2,5-dibromo-1-methoxymethyl-4-nitroimidazole (19.68 g, yield: 84.3%) as yellow powder product.

Workup

  1. customat 10 to 15° C.
  2. customwas turned back to a room temperature
  3. additionwere added
  4. stirringfurther stirred at a room temperature for 1 hour
  5. temperaturecooled
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with an aqueous solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under a reduced pressure
  10. customThus obtained crude crystals
  11. washwere washed with diisopropyl ether
  12. customdried at 50° C. for 24 hours

Sources & evidence

ORD record
ord-f7ddf988c4f344d58fc0c0dcd2637fa8
Source dataset
uspto-grants-2012_03
Patent number
US08129544B2

Reaction notes

Loading…