1-Bromohexane → HCID 131734977, compound

HRID 922654Notes

Reaction equation

HRID 922654 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][CH2:15][CH3:16].Cl.ClC[C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=CC=2)N=1>C(#N)C>[CH2:11]([N:5]1[C:6]2[C:27](=[CH:22][CH:23]=[CH:24][CH:2]=2)[CH:28]=[C:29]([CH3:20])[CH2:4]1)[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[Br-:10].[Cl:1][C:2]1[NH:3][CH:4]=[NH+:5][C:6]=1[Cl:7]

Participants

6

Reactant 4

HCID 81011-BromohexaneHCID 14797Potassium HydroxideHCID 1400184,5-DichloroimidazoleHCID 30838232-(Chloromethyl)quinoline hydrochloride

Product 1

HCID 131734977HCID 131734977, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

4,5-Dichloroimidazole (1.23 g, 9 mmol) will be dissolved into acetonitrile. Potassium hydroxide (0.61 g, 9.9 mmol) will be added and the mixture will be allowed to stir for 0.5 h. 1-bromohexane (9 mmol) will be added and the solution will be allowed to reflux overnight. The solution will be filtered hot to remove a white precipitate (presumed to be KBr). 2-chloromethylquinoline hydrochloride (9 mmol) will be dissolved into acetonitrile along with an equivalent of base. This mixture will be added to the previous mixture and will be returned to reflux overnight. The mixture will be allowed to cool to room temperature, resulting in a yellow/white precipitate.

Workup

  1. temperatureto reflux overnight
  2. filtrationThe solution will be filtered hot
  3. customto remove a white precipitate (presumed to be KBr)
  4. additionThis mixture will be added to the previous mixture
  5. temperatureto reflux overnight
  6. customresulting in a yellow/white precipitate

Sources & evidence

ORD record
ord-8ec6c5cf22f143aabbff5ad9443926c0
Source dataset
uspto-grants-2016_03
Patent number
US09278951B2

Reaction notes

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