1-Bromohexane → HCID 70981889, compound

HRID 922608Notes

Reaction equation

HRID 922608 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].[K+].[Br-].Br[CH2:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=1>C(#N)C>[Br-:10].[CH2:11]([C:29]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[C:21]([CH3:20])[C:30]=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][CH3:16]

Participants

7

Reactant 5

HCID 81011-BromohexaneHCID 14797Potassium HydroxideHCID 703202-BromomethylnaphthaleneHCID 1400184,5-DichloroimidazoleHCID 253877Potassium Bromide

Product 1

HCID 70981889HCID 70981889, compoundYield 65%

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-bromohexane (1.26 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 precipitate (2.57, 65% yield). 1H NMR (500 MHz, DMSO-d6) 9.64 (1H, s, NCHN), 8.02 (4H, m, Ar), 7.57 (3H, m, Ar), 5.66 (2H, s, NCH2), 4.22 (2H, t, NCH2), 1.80 (2H, tt, CH2), 1.30 (6H, m, CH2), 0.93 (3H, t, CH3). 13C{1H} NMR (125 MHz, DMSO-d6) 136.4 (NCN), 132.8 (Ar), 132.6 (Ar), 130.0 (Ar), 128.8 (Ar), 127.8 (Ar), 127.7 (Ar), 127.6 (Ar), 126.8 (Ar), 126.7 (Ar), 125.5 (Ar), 119.1 (Ar), 51.6 (CH2), 48.3 (CH2), 30.5 (CH2), 28.0 (CH2), 24.9 (CH2), 21.8 (CH2), 13.2 (CH3). MS: m/z=332.9 (theor for C20H23Cl2N2Br1=414.17).

Workup

  1. temperatureto reflux overnight
  2. filtrationThe solution was filtered hot
  3. additionwas added
  4. temperatureto reflux overnight
  5. customresulting in a yellow precipitate (2.57, 65% yield)

Sources & evidence

ORD record
ord-0a5d49f4f9f0437882e005c26efbecd0
Source dataset
uspto-grants-2016_03
Patent number
US09278951B2

Reaction notes

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