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

HRID 431916

반응식

HRID 431916 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c4d9b666254e46b88ed6319747e65c2d
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06660753B2

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