Hydrogen Bromide → HCID 86719616, compound

HRID 922622Notes

Reaction equation

HRID 922622 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[Cl:7].[OH-].[K+].[Br:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16].Br[CH2:19][C:20]([OH:22])=[O:21].Br>C(#N)C>[Br-:10].[C:15]([CH2:14][CH2:13][CH2:12][CH2:11][N:3]1[C:2]([Cl:1])=[C:6]([Cl:7])[N+:5]([CH2:19][C:20]([OH:22])=[O:21])=[CH:4]1)([OH:17])=[O:16]

Participants

7

Reactant 5

HCID 260Hydrogen BromideHCID 6227Bromoacetic AcidHCID 14797Potassium HydroxideHCID 163685-Bromovaleric acidHCID 1400184,5-Dichloroimidazole

Product 1

HCID 86719616HCID 86719616, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4,5-dichloroimidazole (1.00 g, 7.36 mmol) was dissolved in acetonitrile. Potassium hydroxide (0.828 g, 14.72 mmol) was added to the solution and allowed to reflux for 30 min. 1 equivalent of 5-bromopentanoic acid (1.33 g, 7.36 mmol) was added to the solution and refluxed for 5 h. Solution was filtered to remove the KBr precipitate and placed back onto reflux. 2-bromoacetic acid (2.15 g, 15.46 mmol) was added to the solution and refluxed for 2.5 h. The solution was neutralized with 6M HBr, volatiles removed in vacuo, and the resulting white precipitate was collected and analyzed. 1H NMR (300 MHz, DMSO-d6): δ 3.11, 3.56, 4.68, 4.91, 5.24, 8.24, 10.06, 12.04.

Workup

  1. temperatureto reflux for 30 min
  2. temperaturerefluxed for 5 h
  3. filtrationSolution was filtered
  4. customto remove the KBr precipitate
  5. temperatureonto reflux
  6. temperaturerefluxed for 2.5 h
  7. customvolatiles removed in vacuo
  8. customthe resulting white precipitate was collected

Sources & evidence

ORD record
ord-c72dad2400d745b2860540539687feb5
Source dataset
uspto-grants-2016_03
Patent number
US09278951B2

Reaction notes

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