Hydrogen Bromide → HCID 86719610, compound

HRID 922618Notes

Reaction equation

HRID 922618 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[Cl:7].[OH-].[K+].[Br:10][CH2:11][C:12]([OH:14])=[O:13].Br[CH2:16][C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=1.Br>C(#N)C>[Br-:10].[C:12]([CH2:11][N:3]1[C:2]([Cl:1])=[C:6]([Cl:7])[N+:5]([CH2:16][C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=2)=[CH:4]1)([OH:14])=[O:13]

Participants

7

Reactant 5

HCID 260Hydrogen BromideHCID 6227Bromoacetic AcidHCID 14797Potassium HydroxideHCID 703202-BromomethylnaphthaleneHCID 1400184,5-Dichloroimidazole

Product 1

HCID 86719610HCID 86719610, 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 2-bromoacetic acid (2.15 g, 15.46 mmol) was added to the solution and refluxed for 2.5 h. Solution was filtered to remove the KBr precipitate and placed back onto reflux. An equivalent of 2-(bromomethyl)naphthalene (1.63 g, 7.36 mmol) was added to 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 4.71, 5.75, 7.59, 8.02, 9.81, 12.71.

Workup

  1. temperatureto reflux for 30 min
  2. temperaturerefluxed for 2.5 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-3a6ae060f0e441f4b5dc5aa4d2f763a5
Source dataset
uspto-grants-2016_03
Patent number
US09278951B2

Reaction notes

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