Methyl 4-(chloromethyl)benzoate → Methyl 4-((1-methyl-3,5-dioxo-1,2,4-triazolidin4-yl)methyl)benzoate

HRID 1180112

反応式

HRID 1180112 の反応式
[CH3:1][N:2]1[C:6](=[O:7])[NH:5][C:4](=[O:8])[NH:3]1.[Na].[CH3:10][O:11][C:12](=[O:21])[C:13]1[CH:18]=[CH:17][C:16]([CH2:19]Cl)=[CH:15][CH:14]=1>CS(C)=O>[CH3:1][N:2]1[C:6](=[O:7])[N:5]([CH2:19][C:16]2[CH:17]=[CH:18][C:13]([C:12]([O:11][CH3:10])=[O:21])=[CH:14][CH:15]=2)[C:4](=[O:8])[NH:3]1

参加物

5

反応物 3

HCID 36664Methyl 4-(chloromethyl)benzoateHCID 1792121-Methyl-1,2,4-triazolidine-3,5-dioneHCID 5360545Sodium

生成物 1

HCID 58978277Methyl 4-((1-methyl-3,5-dioxo-1,2,4-triazolidin4-yl)methyl)benzoate収率 72%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

To a solution of 1-methyl-[1,2,4]triazolidine-3,5-dione (1.886 g, 0.0164 mol) and sodium hyhride (200 mg) in DMSO (5 mL) was added 4-chloromethyl-benzoic acid methyl ester (1.0 g, 0.0054 mol). The mixture was stirred at RT for overnight, quenched with H2O (100 mL), and extracted by CH2Cl2. The organic layer was washed with H2O, dried (Na2SO4) and concentrated in vacuo to yield methyl 4-((1-methyl-3,5-dioxo-1,2,4-triazolidin4-yl)methyl)benzoate (1.02 g, 72%). 1H NMR (CDCl3): 7.93 (d, J=8.4 Hz, 2H), 7.27 (d, J=8.4 Hz, 2H), 4.68 (s, 2H), 3.83 (s, 3H), 3.27 (s, 3H). MS (ESI) m/e: 264 (M++1)

後処理

  1. customquenched with H2O (100 mL)
  2. extractionextracted by CH2Cl2
  3. washThe organic layer was washed with H2O
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-b1ba69038d7549e4a387c422e77bffbb
出典データセット
uspto-grants-2007_10
特許番号
US07279576B2

関連ノート

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