Chlorosuccinimide → HCID 15088597, compound

HRID 439609Notes

Reaction equation

HRID 439609 reaction equation
[Cl:1]N1C(=O)CCC1=O.[C:9]1([C:15]2[NH:16][C:17]([CH2:22][OH:23])=[C:18](CO)[N:19]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.COC(O)C>O1CCOCC1>[C:9]1([C:15]2[NH:16][C:17]([CH2:22][OH:23])=[C:18]([Cl:1])[N:19]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 31398ChlorosuccinimideHCID 1091151H-Imidazole-4,5-dimethanol, 2-phenyl-HCID 30156371-Methoxyethanol

Product 1

HCID 15088597HCID 15088597, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

2.34 Grams (17.5 mmol) of the N-chlorosuccinimide was added to a solution consisting of 3.26 g (16 mmol) of the 2-phenyl-4,5-bis(hydroxymethyl) imidazole, 24 ml of methoxyethanol and 37 ml of dioxane maintained at a temperature of 50° C. with stirring. The mixture was then reacted at the same temperature for 24 hours with stirring, and the reaction solution was concentrated under reduced pressure. The obtained reaction product was washed with water and was recrystallized from propyl alcohol to obtain a 2-phenyl-4-chloro-5-(hydroxymethyl) imidazole in an amount of 1.0 g (yield 30%).

Workup

  1. customThe mixture was then reacted at the same temperature for 24 hours
  2. stirringwith stirring
  3. concentrationthe reaction solution was concentrated under reduced pressure
  4. customThe obtained reaction product
  5. washwas washed with water
  6. customwas recrystallized from propyl alcohol

Sources & evidence

ORD record
ord-286b59d86225441b82b32f8b8a617425
Source dataset
uspto-grants-1996_05
Patent number
US05514811

Reaction notes

Loading…