Water → dimethyl 2-bromo-1-(3-methyl-2-buten-1-yl)-1H-imidazole-4,5-dicarboxylate

HRID 1446040Notes

Reaction equation

HRID 1446040 reaction equation
[Br:1][C:2]1[NH:3][C:4]([C:11]([O:13][CH3:14])=[O:12])=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:6]=1.Br[CH2:16][CH:17]=[C:18]([CH3:20])[CH3:19].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Br:1][C:2]1[N:6]([CH2:16][CH:17]=[C:18]([CH3:20])[CH3:19])[C:5]([C:7]([O:9][CH3:10])=[O:8])=[C:4]([C:11]([O:13][CH3:14])=[O:12])[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 700922-Butene, 1-bromo-3-methyl-HCID 21947693Dimethyl 2-bromo-1H-imidazole-4,5-dicarboxylate

Product 1

HCID 59815068dimethyl 2-bromo-1-(3-methyl-2-buten-1-yl)-1H-imidazole-4,5-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 12.20 g (46 mmol) dimethyl 2-bromo-imidazole-4,5-dicarboxylate, 7.16 g (48 mmol) 1-bromo-3-methyl-2-butene and 7.19 g (52 mmol) potassium carbonate in 150 ml of dimethylformamide were stirred for two hours at 50° C. Then 100 ml of water were added, and the mixture was extracted three times with ethyl acetate. The extracts were dried and evaporated down. The crude product thus obtained was purified by column chromatography (silica gel; eluant: cyclohexane/ethyl acetate 4:1->2:1).

Workup

  1. extractionthe mixture was extracted three times with ethyl acetate
  2. customThe extracts were dried
  3. customevaporated down

Sources & evidence

ORD record
ord-521f677e55724ba598417ab1cb5c91ea
Source dataset
uspto-grants-2010_02
Patent number
US07667035B2

Reaction notes

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