Hydrochloric Acid → HCID 15597006, compound

HRID 2249354Notes

Reaction equation

HRID 2249354 reaction equation
C(O[K])(C)(C)C.[CH3:7][C:8]1[NH:9][CH:10]=[CH:11][N:12]=1.[OH:13][CH:14]([CH2:17][OH:18])[CH2:15]Br.Cl>C(O)(C)(C)C.O1CCCC1>[OH:13][CH:14]([CH2:17][OH:18])[CH2:15][N:9]1[CH:10]=[CH:11][N:12]=[C:8]1[CH3:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 127492-MethylimidazoleHCID 208273-Bromo-1,2-propanediolHCID 178418922HCID 178418922, compound

Product 1

HCID 15597006HCID 15597006, compoundYield 81.2%

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A200 ml flask was charged with 2.0 g of t-butoxypotassium, 70 ml of tetrahydrofuran, 1.23 g of 2-methylimidazole. After stirring for 30 minutes, a solution of 2.5 g of 2,3-dihydroxyl-n-propyl bromide in 5 ml of t-butanol was added. After refluxing for one hour, 5 ml of 1 N HCl solution was added and the mixture was allowed to stand over night. The solvent was evaporated under reduced pressure. The residue was extracted with dichloromethane, washed with saturated aqueous solution of sodium hydrogencarbonate, and dried over anhydrous magnesium sulfate. After removing anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure and the residue was purified by column chromatography (development solvent: methyl acetate/methanol=90/10) to obtain 1.9 g of 1-(2′,3′-dihydroxylpropyl)-2-methylimidazole (compound (A-1)). 1H-NMR spectrum of the resulting compound is shown in FIG. 1.

Workup

  1. temperatureAfter refluxing for one hour
  2. waitto stand over night
  3. customThe solvent was evaporated under reduced pressure
  4. extractionThe residue was extracted with dichloromethane
  5. washwashed with saturated aqueous solution of sodium hydrogencarbonate
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customAfter removing anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customthe residue was purified by column chromatography (development solvent: methyl acetate/methanol=90/10)

Sources & evidence

ORD record
ord-2bed1feeb64e48b9a611cfa7273656a8
Source dataset
uspto-grants-2008_01
Patent number
US07314701B2

Reaction notes

Loading…