Potassium Hydroxide → HCID 70982878, compound

HRID 922604Notes

Reaction equation

HRID 922604 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[Cl:7].[OH-].[K+].I[CH2:11][CH2:12][CH3:13].[K+].[Br-].[Br:16][CH2:17][C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=1>C(#N)C>[Br-:16].[CH2:11]([C:26]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[C:18]([CH3:17])[C:27]=1[N+:3]1[C:2]([Cl:1])=[C:6]([Cl:7])[NH:5][CH:4]=1)[CH2:12][CH3:13]

Participants

7

Reactant 5

HCID 14797Potassium HydroxideHCID 336431-IodopropaneHCID 703202-BromomethylnaphthaleneHCID 1400184,5-DichloroimidazoleHCID 253877Potassium Bromide

Product 1

HCID 70982878HCID 70982878, compoundYield 31%

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-iodopropane (0.88 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 (1.125, 31% yield). 1H NMR (500 MHz, DMSO-d6) 9.58 (1H, s, NCHN), 8.02 (4H, m, Ar), 7.57 (3H, m, Ar), 5.66 (2H, s, NCH2), 4.21 (2H, t, NCH2), 1.85 (2H, tq, CH2), 0.94 (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), 126.9 (Ar), 126.8 (Ar), 125.5 (Ar), 119.1 (Ar), 118.8 (Ar), 51.6 (CH2), 50.0 (CH2), 21.7 (CH2), 10.3 (CH3). MS: m/z=318.8 (theor for C17H17Cl2N2Br1=399.13).

Workup

  1. temperatureto reflux overnight
  2. filtrationThe solution was filtered hot
  3. additionwas added
  4. temperatureto reflux overnight
  5. customresulting in a yellow precipitate (1.125, 31% yield)

Sources & evidence

ORD record
ord-6f4d6b1c2d764bf19f1499853244ddc6
Source dataset
uspto-grants-2016_03
Patent number
US09278951B2

Reaction notes

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