Hydrochloric Acid → (2-Ethyl-6-nitro-2,3-dihydroimidazo[2,1-b][1,3]oxazol-2-yl)methanol

HRID 856167Notes

Reaction equation

HRID 856167 reaction equation
[CH2:1]([C:3]1([CH2:14][O:15]COC)[O:7][C:6]2=[N:8][C:9]([N+:11]([O-:13])=[O:12])=[CH:10][N:5]2[CH2:4]1)[CH3:2].Cl>CO>[CH2:1]([C:3]1([CH2:14][OH:15])[O:7][C:6]2=[N:8][C:9]([N+:11]([O-:13])=[O:12])=[CH:10][N:5]2[CH2:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69479737HCID 69479737, compound

Product 1

HCID 23081317(2-Ethyl-6-nitro-2,3-dihydroimidazo[2,1-b][1,3]oxazol-2-yl)methanolYield 40%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Ethyl-2-methoxymethoxymethyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole prepared in Example 21 (21.5 g, 83.7 mmol) was suspended in methanol (430 ml). Concentrated hydrochloric acid (2.15 ml) was added to this suspension followed by stirring under reflux for 5 hours. The reaction mixture was concentrated under reduced pressure, and the precipitates were filtered off to afford 2-ethyl-2-hydroxymethyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole (7.14 g, yield 40%) as a light yellow powder.

Workup

  1. temperatureunder reflux for 5 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. filtrationthe precipitates were filtered off

Sources & evidence

ORD record
ord-55d867a8565940559a4ce0a9a820ded9
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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