N-bromobutanimide → 2-acetoxy-1-acetyl-5-bromomethyl-1H-imidazole-4-carboxylic acid methyl ester

HRID 1348956Notes

Reaction equation

HRID 1348956 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([O:14][C:15](=[O:17])[CH3:16])[N:8]([C:11](=[O:13])[CH3:12])[C:9]=1[CH3:10])=[O:4].[Br:18]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([O:14][C:15](=[O:17])[CH3:16])[N:8]([C:11](=[O:13])[CH3:12])[C:9]=1[CH2:10][Br:18])=[O:4]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 694325842-acetoxy-1-acetyl-5-methyl-1H-imidazole-4-carboxylic acid methyl ester

Product 1

HCID 865974912-acetoxy-1-acetyl-5-bromomethyl-1H-imidazole-4-carboxylic acid methyl esterYield 99%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 4b (9.0 g, 38 mmol) in 300 mL of CCl4 was added N-bromosuccinimide (7.1 g, 40 mmol) and benzoyl peroxide (80 mg). The solution was refluxed for 4 h and then cooled down to rt. Succinimide was then removed through filtration and the filtrate was concentrated to provide 2-acetoxy-1-acetyl-5-bromomethyl-1H-imidazole-4-carboxylic acid methyl ester 4c (12 g, 95%). MS (ESI+) (M+1)=318.9, 320.9.

Workup

  1. temperatureThe solution was refluxed for 4 h
  2. customSuccinimide was then removed through filtration
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e7e91429b0c3410fb13c036738b34316
Source dataset
uspto-grants-2007_05
Patent number
US07211671B2

Reaction notes

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