Ethyl Bromide → HCID 131734974, compound

HRID 922651Notes

Reaction equation

HRID 922651 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[Cl:7].[OH-].[K+].Br[CH2:11][CH3:12].Cl.ClC[C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=1>C(#N)C>[CH2:16]([N:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:24]=[C:11]([CH3:12])[CH2:2]1)[CH3:25].[Cl-:1].[Cl:1][C:2]1[NH:3][CH:4]=[NH+:5][C:6]=1[Cl:7]

Participants

6

Reactant 4

HCID 6332Ethyl BromideHCID 14797Potassium HydroxideHCID 1400184,5-DichloroimidazoleHCID 30838232-(Chloromethyl)quinoline hydrochloride

Product 1

HCID 131734974HCID 131734974, 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-bromoethane (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-b5043e83158048c3bc6364c33796d5b0
Source dataset
uspto-grants-2016_03
Patent number
US09278951B2

Reaction notes

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