2-Nitroimidazole → 2-[2-Hydroxy-2-(2-nitro-1H-imidazol-1-yl)ethyl]-1H-isoindole-1,3(2H)-dione

HRID 1016690Notes

Reaction equation

HRID 1016690 reaction equation
[O:1]1C[CH:2]1[CH2:3][N:4]1[C:8](=[O:9])[C:7]2=[CH:10][CH:11]=[CH:12][CH:13]=[C:6]2[C:5]1=[O:14].[N+:16]([C:19]1[NH:20][CH:21]=[CH:22][N:23]=1)([O-:18])=[O:17].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[OH:1][CH:2]([N:20]1[CH:21]=[CH:22][N:23]=[C:19]1[N+:16]([O-:18])=[O:17])[CH2:3][N:4]1[C:8](=[O:9])[C:7]2[C:6](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]1=[O:14]

Participants

5

Reactant 3

HCID 107012-NitroimidazoleHCID 11430Potassium CarbonateHCID 21601N-(2,3-Epoxypropyl)phthalimide

Product 1

HCID 223382922-[2-Hydroxy-2-(2-nitro-1H-imidazol-1-yl)ethyl]-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-(2,3-epoxypropyl)phthalimide (1) (Fluka, 25.0 g, 0.123 mol) in ethanol (200 mL), 2-nitroimidazole (2) (Nippon Ghosei, 14.5 g, 0.128 mol) and potassium carbonate (1.5 g) were added, and the reaction mixture was heated under reflux for 8 hrs. The reaction mixture was cooled and the yellow solid obtained was filtered and washed with ethanol (2×75 mL). The precipitate was transferred to a one liter beaker and water was added (500 mL). The mixture was stirred for 15 min. The yellow precipitate was filtered and the solid was washed with water (3×250 mL). 2-[2-hydroxy-2-(2-nitro-1H-imidazol-1-yl)ethyl]-1H-isoindole-1,3(2H)-dione (3) was obtained and dried under vacuum. Yield 32.8 g (85%). The product was pure by proton NMR and HPLC, and was used in the next step without further purification. A portion (˜2 g) of the solid was recrystallized from methanol. The melting point was 213-214° C.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 8 hrs
  3. temperatureThe reaction mixture was cooled
  4. customthe yellow solid obtained
  5. filtrationwas filtered
  6. washwashed with ethanol (2×75 mL)
  7. additionwas added (500 mL)
  8. filtrationThe yellow precipitate was filtered
  9. washthe solid was washed with water (3×250 mL)

Sources & evidence

ORD record
ord-11fdb985991f402aaa9cd69deb3e70e1
Source dataset
uspto-grants-2002_11
Patent number
US06476234B2

Reaction notes

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