Hydrogen Bromide → HCID 14155063, compound

HRID 1382665Notes

Reaction equation

HRID 1382665 reaction equation
N[C:2]1[C:3]([CH2:20][CH3:21])=[C:4]([N:10]2[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][N:12]=[CH:11]2)[C:5]([CH2:8][CH3:9])=[CH:6][CH:7]=1.[BrH:22].N([O-])=O.[Na+].N([O-])=O.NC(N)=O>O.[Cu](Br)Br.C(O)(=O)C>[Br:22][C:2]1[C:3]([CH2:20][CH3:21])=[C:4]([N:10]2[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][N:12]=[CH:11]2)[C:5]([CH2:8][CH3:9])=[CH:6][CH:7]=1

Participants

9

Reactant 5

HCID 260Hydrogen BromideHCID 946NitriteHCID 1176UreaHCID 14155062HCID 14155062, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 14155063HCID 14155063, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 24611Copper bromide (CuBr2)CatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

20 g (0.07 mol) of ethyl 1-(3-amino-2,6-diethylphenyl)imidazole-5-carboxylate were added to a mixture of 30 ml of concentrated hydrobromic acid, 30 ml of glacial acetic acid and 30 ml of water, the mixture was cooled to 0° C., and a solution of 12.0 g (0.17 mol) of sodium nitrite in 15 ml of water was added dropwise at this temperature. After 30 minutes at 0° C., the excess nitrite was decomposed using urea, and the solution was added dropwise at 0° C. to a copper bromide solution (prepared by conventional processes from 24.9 g of copper sulfate, 15.5 g of sodium bromide, 6.3 g of sodium sulfite, 80 ml of water and 40 ml of concentrated hydrobromic acid). The reaction mixture was allowed to warm to room temperature and was neutralized, the product was extracted with methylene chloride, and the organic phase was washed with water, dried over sodium sulfate and evaporated. After chromatographic purification, 17.4 g (71% of theory) of ethyl 1-(3-bromo-2,6-diethylphenyl)-imidazole-5-carboxylate were obtained as a pale yellow oil. Identification was effected by 1H NMR spectroscopy.

Workup

  1. temperatureto warm to room temperature
  2. extractionthe product was extracted with methylene chloride
  3. washthe organic phase was washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customAfter chromatographic purification

Sources & evidence

ORD record
ord-e9937f6a3932472bbdf0f5cc029fa0c6
Source dataset
uspto-grants-1989_02
Patent number
US04808213

Reaction notes

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