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

HRID 594096

反応式

HRID 594096 の反応式
[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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 73012-Methyltetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-2b88c0b3ac904468af3e754542607881
出典データセット
uspto-grants-2016_01
特許番号
US09242972B2

関連ノート

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