Acetonitrile → HCID 70982319, compound

HRID 922605Notes

Reaction equation

HRID 922605 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[Cl:7].[OH-].[K+].I[CH:11]([CH3:13])[CH3:12].[K+].[Br-].[Br:16]C[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:28](#N)C>>[Br-:16].[CH2:11]([C:13]1[C:22]([CH3:23])=[CH:21][C:20]2[C:25](=[CH:26][CH:27]=[CH:18][CH:19]=2)[C:24]=1[N+:3]1[C:2]([Cl:1])=[C:6]([Cl:7])[NH:5][CH:4]=1)[CH2:12][CH3:28]

Participants

7

Reactant 6

HCID 6342AcetonitrileHCID 6362Isopropyl iodideHCID 14797Potassium HydroxideHCID 703202-BromomethylnaphthaleneHCID 1400184,5-DichloroimidazoleHCID 253877Potassium Bromide

Product 1

HCID 70982319HCID 70982319, compoundYield 36%

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. 2-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 white crystalline solid (1.33 g, 36% yield). 1H NMR (500 MHz, DMSO-d6) 9.82 (1H, s, NCHN), 7.99 (4H, m, Ar), 7.57 (3H, m, Ar), 5.66 (2H, s, NCH2), 4.71 (1H, 5, NCH), 10.94 (6H, 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=397.99).

Workup

  1. temperatureto reflux overnight
  2. filtrationThe solution was filtered hot
  3. additionwas added
  4. temperatureto reflux overnight

Sources & evidence

ORD record
ord-a33b860402ce4daf9a3d8910bdcfb723
Source dataset
uspto-grants-2016_03
Patent number
US09278951B2

Reaction notes

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