Bromoform → HCID 15461785, compound

HRID 566434Notes

Reaction equation

HRID 566434 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-ae1c7be0849e4aad9a0ec9ac6aababc4
Source dataset
uspto-grants-2001_01
Patent number
US06174906B1

Reaction notes

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