Potassium Hydroxide → HCID 86719582, compound

HRID 922598Notes

Reaction equation

HRID 922598 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[Cl:7].[OH-].[K+].[Br:10][CH2:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=1>C(#N)C>[Br-:10].[Cl:1][C:2]1[N:3]([CH2:11][C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=2)[CH2:4][NH+:5]([CH2:11][C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=2)[C:6]=1[Cl:7]

Participants

5

Reactant 3

HCID 14797Potassium Hydroxide2×HCID 703202-BromomethylnaphthaleneHCID 1400184,5-Dichloroimidazole

Product 1

HCID 86719582HCID 86719582, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

4,5-dichloroimidazole (10.0 mmol, 1.370 g) and KOH (11.0 mmol, 0.617 g) were placed in a 50 mL round bottom flask with 10 mL acetonitrile. The mixture was brought to reflux (85° C.) and stirred 1 h until KOH was consumed. 2-Bromomethylnapthalene (10.00 mmol, 2.211 g) was added and the solution was stirred 2.5 hours. KBr was removed by vacuum filtration and a second equivalent of bromomethylnapthalene was added to the filtrate. The mixture was stirred at reflux for 1.5 hours. The white precipitate was collected by filtration and analyzed. Yield: 92.0% 1H NMR (500 MHz, d6-DMSO): δ 5.71 (s, 4H), 7.57-7.62 (m, 6H), 7.95-8.06 (m, 8H), 9.75 (s, 1H) ppm. 13C NMR (500 MHz, d6-DMSO): δ 51.8, 117.9, 119.3, 125.5, 136.7, 136.8, 127.7, 127.8, 128.8, 130.1, 132.7, 132.8, 136.9 ppm.

Workup

  1. customwas consumed
  2. customKBr was removed by vacuum filtration
  3. additiona second equivalent of bromomethylnapthalene was added to the filtrate
  4. stirringThe mixture was stirred
  5. temperatureat reflux for 1.5 hours
  6. filtrationThe white precipitate was collected by filtration

Sources & evidence

ORD record
ord-8dae6096dd4248c19f4111548c3e3a18
Source dataset
uspto-grants-2016_03
Patent number
US09278951B2

Reaction notes

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