Bromoform → HCID 15461785, compound

HRID 378232Notes

Reaction equation

HRID 378232 reaction equation
N[C:2]1[N:6]([CH2:7][CH2:8][CH2:9][CH3:10])[CH:5]=[N:4][C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12].N(OCCCC)=O.C(Br)(Br)[Br:24]>>[Br:24][C:2]1[N:6]([CH2:7][CH2:8][CH2:9][CH3:10])[CH:5]=[N:4][C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

4

Reactant 3

HCID 5558BromoformHCID 10996Butyl nitriteHCID 7230647HCID 7230647, compound

Product 1

HCID 15461785HCID 15461785, compoundYield 46%

Procedure

To a solution of ethyl 5-amino-1-n-butyl-1H-imidazole-4-carboxylate (0.05 g, 0.24 mmol) in bromoform (5 mL) was added butyl nitrite (0.10 mL, 0.71 mmol). The reaction mixture was stirred at reflux for 5 h. After an aqueous work up, extracting with ethyl acetate, the combined organic extracts were washed with brine and dried (Na2SO4). After removing the solvent under reduced pressure, flash column chromatography (1:1 ether/hexane) of the residue gave the title compound as an oil (0.03 g, 46%). 1H NMR (250 MHz, CDCl3)δ 7.50 (b, 1H), 4.41 (q, 2H), 3.95 (t, 2H), 1.70 (quintet, 2H), 1.40 (m, 5H), 1.00 (t, 3H).

Workup

  1. temperatureat reflux for 5 h
  2. extractionAfter an aqueous work up, extracting with ethyl acetate
  3. washthe combined organic extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. customAfter removing the solvent under reduced pressure, flash column chromatography (1:1 ether/hexane) of the residue

Sources & evidence

ORD record
ord-82c1533f427c49dd8f7f66f89755b42b
Source dataset
uspto-grants-2000_02
Patent number
US06030970

Reaction notes

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