Acetonitrile → HCID 70982063, compound

HRID 922611Notes

Reaction equation

HRID 922611 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[Cl:7].[OH-].[K+].C(#N)C.Br[CH2:14][CH:15]1[O:20][C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[O:17][CH2:16]1>C(OCC)C>[O:20]1[C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[O:17][CH2:16][CH:15]1[CH2:14][N:3]1[C:2]([Cl:1])=[C:6]([Cl:7])[N:5]=[CH:4]1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 14797Potassium Hydroxide2×HCID 983332-Bromomethyl-1,4-benzodioxaneHCID 1400184,5-Dichloroimidazole

Product 1

HCID 70982063HCID 70982063, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4,5-Dichloroimidazole (0.68 g, 5 mmol) and potassium hydroxide (0.28 g, 5 mmol) were added to a round bottom flask. Acetonitrile (2 mL) was added and the mixture was brought to reflux and stirred 30 min until all KOH was consumed. 2-(Bromomethyl)-1,4-benzodioxane (1.5 mL, 10 mmol) was added and the solution was returned to reflux overnight, during which time a white precipitate formed. The mixture was cooled to ambient temperature and filtered to remove the precipitate. The filtrate was concentrated via rotary evaporation at 75° C. until a yellow liquid remained. Upon cooling, the solution yielded a yellow solid. The solid was stirred in diethyl ether and filtered to yield a pale yellow solid (0.73 g, 52% yield).

Workup

  1. temperatureto reflux
  2. customwas consumed
  3. temperatureto reflux overnight, during which time a white precipitate
  4. customformed
  5. filtrationfiltered
  6. customto remove the precipitate
  7. concentrationThe filtrate was concentrated via rotary evaporation at 75° C. until a yellow liquid
  8. temperatureUpon cooling
  9. customthe solution yielded a yellow solid
  10. filtrationfiltered

Sources & evidence

ORD record
ord-9f67b96068f24b7395e478a674119f78
Source dataset
uspto-grants-2016_03
Patent number
US09278951B2

Reaction notes

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