Lithium iodide → 3-[(Dipropylamino)carbonyl]-5-(5-methyl-1,2,4-oxadiazol-3-yl)benzoic Acid

HRID 14060

反応式

HRID 14060 の反応式
[CH2:1]([N:4]([CH2:23][CH2:24][CH3:25])[C:5]([C:7]1[CH:8]=[C:9]([CH:14]=[C:15]([C:17]2[N:21]=[C:20]([CH3:22])[O:19][N:18]=2)[CH:16]=1)[C:10]([O:12]C)=[O:11])=[O:6])[CH2:2][CH3:3].[I-].[Li+]>N1C=CC=CC=1>[CH2:23]([N:4]([CH2:1][CH2:2][CH3:3])[C:5]([C:7]1[CH:8]=[C:9]([CH:14]=[C:15]([C:17]2[N:21]=[C:20]([CH3:22])[O:19][N:18]=2)[CH:16]=1)[C:10]([OH:12])=[O:11])=[O:6])[CH2:24][CH3:25]

参加物

4

反応物 2

HCID 66321Lithium iodideHCID 21086176Methyl 3-[(dipropylamino)carbonyl]-5-(5-methyl-1,2,4-oxadiazol-3-yl)benzoate

生成物 1

HCID 210857883-[(Dipropylamino)carbonyl]-5-(5-methyl-1,2,4-oxadiazol-3-yl)benzoic Acid

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

A stirred solution of methyl 3-[(dipropylamino)carbonyl]-5-(5-methyl-1,2,4-oxadiazol-3-yl)benzoate (629 mg, 1.8 mmol) and lithium iodide (2.4 g, 18 mmol) in pyridine (7 ml) is refluxed for 18 h. The reaction mixture is cooled to room temperature and the solvent is concentrated under reduced pressure. The residue is dissolved in water, washed with ethyl acetate, the aqueous layer is acidified to pH 3 with 1 N hydrochloric acid and extracted with chloroform (3×100 mL). The organic layer is dried (sodium sulfate), filtered, and concentrated to give the title compound. 1H NMR (500 MHz, CDCl3) δ 11.11 (br s, 1H), 8.85 (t, J=1 Hz, 1H), 8.31 (t, J=1 Hz, 1H), 8.23 (t, J=1 Hz, 1H), 3.51 (s, 2H), 3.19 (s, 2H), 2.72 (s, 3H), 1.73 (d, J=7 Hz, 2H), 1.56 (d, J=7 Hz, 2H), 1.01 (t, J=7 Hz, 3H), 0.76 (t, J=7 Hz, 3H).

後処理

  1. concentrationthe solvent is concentrated under reduced pressure
  2. dissolutionThe residue is dissolved in water
  3. washwashed with ethyl acetate
  4. extractionextracted with chloroform (3×100 mL)
  5. dry with materialThe organic layer is dried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-7b79faa8ffc54fb9895d4a4bd7a226ad
出典データセット
uspto-grants-2010_06
特許番号
US07727997B2

関連ノート

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