Imidazole → HCID 57815688, compound

HRID 1664074Notes

Reaction equation

HRID 1664074 reaction equation
[H-].[Na+].[CH3:3][CH:4]([CH2:13][CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:5][CH2:6][O:7][CH2:8][CH2:9][CH2:10][CH2:11]Br.[NH:19]1[CH:23]=[CH:22][N:21]=[CH:20]1>C(Cl)(Cl)Cl>[CH3:3][CH:4]([CH2:13][CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:5][CH2:6][O:7][CH2:8][CH2:9][CH2:10][CH2:11][N:19]1[CH:23]=[CH:22][N:21]=[CH:20]1

Participants

5

Reactant 3

HCID 795Imidazole3×HCID 24758Sodium hydrideHCID 57815684HCID 57815684, compound

Product 1

HCID 57815688HCID 57815688, compoundYield 118.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Sodium hydride (1.79 g 60% dispersion in oil, 1.07 g, 44.8 mmol) was weighed out in a 250 mL round bottom flask. The mineral oils were washed out with hexane (3×15 mL). DMF (30 mL) was added, followed by (3,7-dimethyloctanyl)oxybutyl bromide (3 g, 10.2 mmol) and then the reaction mixture was stirred at room temperature under N2 for a couple of minutes. Imidazole (3.50 g, 51.4 mmol) was added in portions while cooling the reaction mixture in an ice bath. The addition of the imidazole was exothermic causing the mixture to become a milky off-white and then clear yellow in colour after complete addition of the imidazole. Stirring was continued under N2 at room temperature for 3 d. The reaction mixture was diluted with chloroform (100 mL) to form a thick cloudy mixture and washed with water (2×50 mL). The organic layer was dried (Na2SO4) and the solvent was removed at reduced pressure and then under high vacuum to give the product as a brown clear oil (3.38 g).

Workup

  1. washThe mineral oils were washed out with hexane (3×15 mL)
  2. additionDMF (30 mL) was added
  3. temperaturewhile cooling the reaction mixture in an ice bath
  4. stirringStirring
  5. customto form a thick cloudy mixture
  6. washwashed with water (2×50 mL)
  7. dry with materialThe organic layer was dried (Na2SO4)
  8. customthe solvent was removed at reduced pressure

Sources & evidence

ORD record
ord-6cb3edbc033e4aaeac144cbcb3008b31
Source dataset
uspto-grants-2011_10
Patent number
US08038737B2

Reaction notes

Loading…