Acetic Acid → HCID 14621554, compound

HRID 2372393Notes

Reaction equation

HRID 2372393 reaction equation
[CH2:1]1[N:3]([CH2:4][CH:5]([OH:15])[CH2:6][N:7]2[C:11]([N+:12]([O-:14])=[O:13])=[N:10][CH:9]=[CH:8]2)[CH2:2]1.[C:16]([OH:19])(=[O:18])[CH3:17].C.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[N+:12]([C:11]1[N:7]([CH2:6][CH:5]([OH:15])[CH2:4][NH:3][CH2:1][CH2:2][O:19][C:16](=[O:18])[CH3:17])[CH:8]=[CH:9][N:10]=1)([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 297MethaneHCID 11430Potassium CarbonateHCID 100153α-(1-Aziridinylmethyl)-2-nitro-1H-imidazole-1-ethanol

Product 1

HCID 14621554HCID 14621554, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 1-(2-nitro-1-imidazolyl)-3-(1-aziridino)-2-propanol (2.12 g, 10.0 mmol) in acetone (20 cm3) prepared as described in Example 1(a) was treated with ethanoic acid (2.5 mol equivalents) at 25° C. then warmed to 50° C. for 15 minutes. The resulting mixture was cooled to 20° C., stirred with decolourising charcoal (0.3 g) and excess anhydrous potassium carbonate for 30 minutes, filtered and concentrated under reduced pressure to give 1-(2-nitro-1-imidazolyl)-3-(2-acetoxyethylamino)-2-propanol (1.58 g, 58.0%) in the form of a pale yellow crystalline solid.

Workup

  1. temperatureThe resulting mixture was cooled to 20° C.
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0f9b643ce62d4e728acb0b4d719a90ad
Source dataset
uspto-grants-1992_03
Patent number
US05098921

Reaction notes

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