Potassium Carbonate → Dimethyl 2-bromo-1H-imidazole-4,5-dicarboxylate

HRID 2116774Notes

Reaction equation

HRID 2116774 reaction equation
[Br:1]Br.[NH:3]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([C:12]([O:14][CH3:15])=[O:13])[N:5]=[CH:4]1.C(=O)([O-])[O-].[K+].[K+]>ClCCl.C(#N)C>[Br:1][C:4]1[NH:3][C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([C:12]([O:14][CH3:15])=[O:13])[N:5]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 24408BromineHCID 768101H-Imidazole-4,5-dicarboxylic acid, 4,5-dimethyl ester

Product 1

HCID 21947693Dimethyl 2-bromo-1H-imidazole-4,5-dicarboxylate

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent2×

Procedure

At ambient temperature 9.50 g (59.45 mmol) bromine were added dropwise to a solution of 9.90 g (53.76 mmol) dimethyl imidazole-4,5-dicarboxylate in 300 ml dichloromethane and 80 ml acetonitrile. 7.46 g (54.00 mmol) potassium carbonate was added, and the reaction mixture was stirred for 2 hours at ambient temperature. Then the dichloromethane was eliminated using the rotary evaporator and the residue was combined with a saturated solution of sodium chloride and sodium thiosulphate. It was extracted ten times with ethyl acetate, the organic extracts were dried over sodium sulphate and then the solvent was eliminated.

Workup

  1. customthe rotary evaporator
  2. extractionIt was extracted ten times with ethyl acetate
  3. dry with materialthe organic extracts were dried over sodium sulphate

Sources & evidence

ORD record
ord-9bc63520a86c4283b7eaa207a0e82e99
Source dataset
uspto-grants-2008_10
Patent number
US07439370B2

Reaction notes

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