Triethylamine → 3-(2-Pyridyl)-5-(3-cyano-5-nitrophenyl)-1,2,4-oxadiazole

HRID 431916

反応式

HRID 431916 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[C:6](Cl)=[O:7])#[N:2].[C:15]([C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([N+:26]([O-])=O)C=1)C(O)=O)#[N:16].C([N:31](CC)CC)C>ClCCl>[N:26]1[CH:24]=[CH:23][CH:19]=[CH:18][C:17]=1[C:15]1[N:16]=[C:6]([C:5]2[CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=[C:3]([C:1]#[N:2])[CH:4]=2)[O:7][N:31]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 219424583-Cyano-5-nitrobenzoyl chlorideHCID 219425653-Cyano-5-nitrobenzoic acid

生成物 1

HCID 219425113-(2-Pyridyl)-5-(3-cyano-5-nitrophenyl)-1,2,4-oxadiazole収率 50%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Using the general procedure for the preparation of acid chlorides, 3-cyano-5-nitrobenzoyl chloride was prepared from 3-cyano-5-nitrobenzoic acid (1.0 g, 5.1 mmol). A solution of the acid chloride in dichloromethane (5 mL) at 0° C. was treated with pyrid-2-ylamidoxime (700 mg, 5.1 mMol) and triethylamine (2.1 mL, 15.3 mmol) and then stirred at ambient temperature for 1 hour. The reaction mixture was washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was dissolved in N,N-dimethylformamide (5 mL) and heated at 110° C. for 4 hours. Standard work up and silica gel chromatography using hexanes:ethyl acetate:dichloromethane (3.5:0.5:4) afforded 149 mg (50%) of 3-(2-pyridyl)-5-(3-cyano-5-nitrophenyl)-1,2,4-oxadiazole: 1H NMR (CDCl3), 6 (ppm): 9.35 (d, 1H), 8.91 (s, 1H), 8.89 (d, 1H), 8.75 (s,1H), 8.26 (d, 1H), 7.94 (m, 1H), 7.53 (m, 1H).

後処理

  1. washThe reaction mixture was washed with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in N,N-dimethylformamide (5 mL)
  6. temperatureheated at 110° C. for 4 hours

出典と根拠

ORDレコード
ord-c4d9b666254e46b88ed6319747e65c2d
出典データセット
uspto-grants-2003_12
特許番号
US06660753B2

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