Diisopropylethylamine → dimethyl 2-bromo-1-(but-2-ynyl)-1H-imidazole-4,5-dicarboxylate

HRID 2214453Notes

Reaction equation

HRID 2214453 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][C:17]#[C:18][CH3:19].C(N(CC)C(C)C)(C)C>O1CCCC1>[Br:1][C:2]1[N:6]([CH2:16][C:17]#[C:18][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

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27568621-Bromo-2-butyneHCID 21947693Dimethyl 2-bromo-1H-imidazole-4,5-dicarboxylate

Product 1

HCID 21947677dimethyl 2-bromo-1-(but-2-ynyl)-1H-imidazole-4,5-dicarboxylateYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 15.0 g (57.0 mmol) of dimethyl 2-bromo-imidazole-4,5-dicarboxylate, 5.15 ml (57.0 mmol) of 1-bromo-2-butyne and 50 ml of N,N-diisopropylethylamine in 280 ml of tetrahydrofuran was refluxed for one hour. The mixture was concentrated by evaporation, the residue combined with approx. 100 ml of water and extracted three times with 70 ml of ethyl acetate. The extracts were washed with 50 ml of water, dried and evaporated down. The crude product thus obtained was purified by column chromatography (silica gel; eluant:dichloromethane with 0–2% ethanol).

Workup

  1. concentrationThe mixture was concentrated by evaporation
  2. extractionextracted three times with 70 ml of ethyl acetate
  3. washThe extracts were washed with 50 ml of water
  4. customdried
  5. customevaporated down

Sources & evidence

ORD record
ord-1681f51638fe4406856b882f7bcf841e
Source dataset
uspto-grants-2006_09
Patent number
US07109192B2

Reaction notes

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