1-Bromononane → HCID 70982815, compound

HRID 922610Notes

Reaction equation

HRID 922610 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][CH2:16][CH2:17][CH2:18][CH3:19].[K+].[Br-].Br[CH2:23][C:24]1[CH:33]=[CH:32][C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=1>C(#N)C>[Br-:10].[CH2:11]([C:32]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[C:24]([CH3:23])[C:33]=1[N+:3]1[C:2]([Cl:1])=[C:6]([Cl:7])[NH:5][CH:4]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

7

Reactant 5

HCID 127421-BromononaneHCID 14797Potassium HydroxideHCID 703202-BromomethylnaphthaleneHCID 1400184,5-DichloroimidazoleHCID 253877Potassium Bromide

Product 1

HCID 70982815HCID 70982815, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4,5-Dichloroimidazole (1.23 g, 9 mmol) was dissolved into 27 mL of acetonitrile. Potassium hydroxide (0.61 g, 9.9 mmol) was added and the mixture was allowed to stir for 0.5 h. 1-bromononane (1.72 mL, 9 mmol) was added and the solution was allowed to reflux overnight. The solution was filtered hot to remove a white precipitate (presumed to be KBr) and 2-bromomethylnaphthalene (1.98 g, 9 mmol) was added and the mixture was returned to reflux overnight. The mixture was then allowed to cool to room temperature, resulting in a yellow/white precipitate (2.73, 56% yield). 1H NMR (500 MHz, DMSO-d6) 9.63 (1H, s, NCHN), 7.99 (4H, m, Ar), 7.58 (3H, m, Ar), 5.66 (2H, s, NCH2), 4.22 (2H, t, NCH2), 1.82 (2H, tt, CH2), 1.25 (12H, m, CH2), 0.93 (3H, t, CH3). MS: m/z=402.8 (theor for C23H29Cl2N2Br1=484.31).

Workup

  1. temperatureto reflux overnight
  2. filtrationThe solution was filtered hot
  3. additionwas added
  4. temperatureto reflux overnight
  5. customresulting in a yellow/white precipitate (2.73, 56% yield)

Sources & evidence

ORD record
ord-5d65d18ef2724e50a5cd10775027e35f
Source dataset
uspto-grants-2016_03
Patent number
US09278951B2

Reaction notes

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