Potassium Carbonate → 2-Methyl-2-(3-hydroxypropyl)-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole

HRID 856169Notes

Reaction equation

HRID 856169 reaction equation
C([O:4][CH2:5][CH2:6][CH2:7][C:8]1([CH3:19])[O:12][C:11]2=[N:13][C:14]([N+:16]([O-:18])=[O:17])=[CH:15][N:10]2[CH2:9]1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:19][C:8]1([CH2:7][CH2:6][CH2:5][OH:4])[O:12][C:11]2=[N:13][C:14]([N+:16]([O-:18])=[O:17])=[CH:15][N:10]2[CH2:9]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 230812032-(3-Acetoxypropyl)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole

Product 1

HCID 230814842-Methyl-2-(3-hydroxypropyl)-6-nitro-2,3-dihydroimidazo[2,1-b]oxazoleYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-(3-acetoxypropyl)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole prepared in Example 30 (3.2 g, 11.88 mmol), potassium carbonate (320 mg, 2.32 mmol) and methanol (35 ml) was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride/methanol=25/1) to afford 2-methyl-2-(3-hydroxypropyl)-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole (2.1 g, 78%) as a light yellow powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (methylene chloride/methanol=25/1)

Sources & evidence

ORD record
ord-eae3bda19cc343e9a566beab7bce889e
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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