Water → 1-(3-Phthalimido-2-hydroxy propyl)-2-nitroimidazole

HRID 1779746Notes

Reaction equation

HRID 1779746 reaction equation
[O:1]1[CH2:15][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+].O>C(O)C>[C:8]1(=[O:9])[N:4]([CH2:3][CH:2]([OH:1])[CH2:15][N:20]2[CH:21]=[CH:22][N:23]=[C:19]2[N+:16]([O-:18])=[O:17])[C:5](=[O:14])[C:6]2=[CH:13][CH:12]=[CH:11][CH:10]=[C:7]12

Participants

6

Reactant 4

HCID 962WaterHCID 107012-NitroimidazoleHCID 11430Potassium CarbonateHCID 21601N-(2,3-Epoxypropyl)phthalimide

Product 1

HCID 3373341-(3-Phthalimido-2-hydroxy propyl)-2-nitroimidazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-(2,3-epoxypropyl)phthalimide (commercially available, 20.3 g, 0.1 mol) in ethanol (200 mL), 2-nitroimidazole (11.3 g, 0.1 mol) and potassium carbonate (1.2 g) were added and the reaction mixture was refluxed for 6 hrs. The reaction mixture was cooled and poured into water (700 ml) and the yellow solid formed was filtered and dried. Yield 28.2 g) 89%). It was recrystallized from methanol. mp. 213°-214° C. 1H NMR (DMSO) ε 3.62 (m, 4H, PhthNCH2CHOH), 4.08 (m, 1H, CHOH), 4.32 and 4.63 (m, 2H, CHOHCH2N<), 5.54 (d, 1H, CHOH), 7.15 and 7.68 (s, 2H, imiH), 7.8 (m, 4H, ArH). MS: (M+H)+ =317+Anal. Calcd. for C14H12N4O5 : C, 53.17; H, 3.82; N, 17.71. Found C, 53.11; H, 3.76; N, 17.49.

Workup

  1. temperaturethe reaction mixture was refluxed for 6 hrs
  2. temperatureThe reaction mixture was cooled
  3. customthe yellow solid formed
  4. filtrationwas filtered
  5. customdried
  6. customIt was recrystallized from methanol

Sources & evidence

ORD record
ord-8eef1c1923fb49d380ef7f8c16066d68
Source dataset
uspto-grants-1997_05
Patent number
US05627286

Reaction notes

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