Hydrogen Bromide → HCID 86719714, compound

HRID 922675Notes

Reaction equation

HRID 922675 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[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][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[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][CH:18]=2)=[CH:4]1)([OH:14])=[O:13]

Participants

7

Reactant 5

HCID 260Hydrogen BromideHCID 6227Bromoacetic AcidHCID 14797Potassium HydroxideHCID 1378441-(Bromomethyl)naphthaleneHCID 1400184,5-Dichloroimidazole

Product 1

HCID 86719714HCID 86719714, 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 1-(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 product will be collected and analyzed.

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 product will be collected

Sources & evidence

ORD record
ord-172a0f5eb8654090945dc98cf9d6d4ab
Source dataset
uspto-grants-2016_03
Patent number
US09278951B2

Reaction notes

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