2-Chlorobenzoxazole → (R)-2-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethoxy)benzoxazole

HRID 856175Notes

Reaction equation

HRID 856175 reaction equation
[H-].[Na+].[OH:3][CH2:4][C@:5]1([CH3:16])[O:9][C:8]2=[N:10][C:11]([N+:13]([O-:15])=[O:14])=[CH:12][N:7]2[CH2:6]1.Cl[C:18]1[O:19][C:20]2[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=2[N:22]=1>CN(C=O)C>[CH3:16][C@@:5]1([CH2:4][O:3][C:18]2[O:19][C:20]3[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=3[N:22]=2)[O:9][C:8]2=[N:10][C:11]([N+:13]([O-:15])=[O:14])=[CH:12][N:7]2[CH2:6]1

Participants

5

Reactant 3

HCID 119862-ChlorobenzoxazoleHCID 24758Sodium hydrideHCID 26596862(r)-(2-Methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-yl)methanol

Product 1

HCID 69482360(R)-2-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethoxy)benzoxazoleYield 24%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (0.1 g, 2.4 mmol) was added to a solution of (R)-2-hydroxymethyl-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole prepared in Example 37 (0.40 g, 2.0 mmol) in DMF (4 ml) followed by stirring for 30 minutes with cooling on ice-bath. To the reaction mixture, 2-chlorobenzoxazole (0.38 g, 2.4 mmol) in DMF (4 ml) was added with cooling on ice-bath followed by stirring at room temperature for 48 hours. Ice-water was added to the reaction mixture. The precipitates were filtered off, washed with water, and then recrystallized from acetonitrile-isopropanol to afford (R)-2-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethoxy)benzoxazole (0.15 g, yield 24%) as a light yellow solid.

Workup

  1. temperaturewith cooling on ice-bath
  2. temperaturewith cooling on ice-bath
  3. stirringby stirring at room temperature for 48 hours
  4. filtrationThe precipitates were filtered off
  5. washwashed with water
  6. customrecrystallized from acetonitrile-isopropanol

Sources & evidence

ORD record
ord-9dbcbf8a498c4404a3182866faed7f8f
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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