Sodium hydride → 3-(6-Methyl-5-nitro-2-pyridinyl)-1,3-oxazolidin-2-one

HRID 594096Notes

Reaction equation

HRID 594096 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][OH:11])[CH:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[C:15](N1C=CN=C1)(N1C=CN=C1)=[O:16].[H-].[Na+]>CC1CCCO1.O.C(OCC)(=O)C>[CH3:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:9][CH2:10][O:11][C:15]2=[O:16])[CH:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 112178252-((6-Methyl-5-nitropyridin-2-yl)amino)ethanol

Product 1

HCID 898762173-(6-Methyl-5-nitro-2-pyridinyl)-1,3-oxazolidin-2-oneYield 84.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 73012-MethyltetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-((6-methyl-5-nitropyridin-2-yl)amino)ethanol (223 mg, 1.131 mmol) in 2-methyltetrahydrofuran (20 mL) was added 1,1′-carbonyldiimidazole (CDI) (220 mg, 1.357 mmol) and the reaction mixture stirred under nitrogen for 4 hours. The mixture was then left to stand for 20 hours. To this was added sodium hydride (60% wt in mineral oil) (100 mg, 2.488 mmol) and the reaction mixture stirred at room temperature for 2 hours. The reaction mixture was then diluted with water and ethyl acetate and the organic phase separated, washed with brine, then dried over magnesium sulphate. The solvent was removed in vacuo and the residue purified by flash silica (Si) chromatography (0-100% ethyl acetate-cyclohexane gradient) to give the title compound (0.213 g) as an off-white solid. LCMS (2 min, formic) Rt 0.85 min, m/z (ES+) 224 (M+H).

Workup

  1. waitThe mixture was then left
  2. waitto stand for 20 hours
  3. stirringthe reaction mixture stirred at room temperature for 2 hours
  4. customthe organic phase separated
  5. washwashed with brine
  6. dry with materialdried over magnesium sulphate
  7. customThe solvent was removed in vacuo
  8. customthe residue purified by flash silica (Si) chromatography (0-100% ethyl acetate-cyclohexane gradient)

Sources & evidence

ORD record
ord-2b88c0b3ac904468af3e754542607881
Source dataset
uspto-grants-2016_01
Patent number
US09242972B2

Reaction notes

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