Sodium Hydroxide → HCID 178440163, compound

HRID 1707767Notes

Reaction equation

HRID 1707767 reaction equation
[OH:1][CH2:2][C:3]1[NH:7][C:6]([CH2:8][CH2:9][CH3:10])=[N:5][C:4]=1[I:11].[OH-].[Na+]>C(O)(=O)C.O>[I:11][C:4]1[N:5]=[C:6]([CH2:8][CH2:9][CH3:10])[NH:7][C:3]=1[CH:2]=[O:1]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 18962498HCID 18962498, compound

Product 1

HCID 178440163HCID 178440163, compoundYield 84.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 35.8 g of 5-hydroxymethyl-4-iodo-2-n-propylimidazole in 325 mL of glacial acetic acid at 20° C. was added dropwise over 1 h 290 mL of 1.0N aqueous ceric ammonium nitrate solution. The resulting mixture was stirred at 20° C. for 1 h. The reaction mixture then was diluted with water, adjusted to pH 5-6 employing aqueous sodium hydroxide solution, and extracted with chloroform. The combined organic phases were washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The resulting crude solid was recrystallized from 1-chlorobutane to furnish 29.9 g of product as a light yellow solid: mp 141°-142° C. NMR (CDCl3) δ 11.51 (br s,1H); 9.43 (s,1H); 2.81 (t,2H); 1.81 (sext., 2H); 0.97 (t,3H). ##STR84##

Workup

  1. extractionextracted with chloroform
  2. washThe combined organic phases were washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting crude solid was recrystallized from 1-chlorobutane

Sources & evidence

ORD record
ord-8aa1fd76fb5046e58565730fd3ddc6f3
Source dataset
uspto-grants-1994_10
Patent number
US05354867

Reaction notes

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