4-Hydroxybenzoic acid hydrazide → 4-Hydroxy-benzoic acid (5-ethyl-thiophen-2-ylmethylene)-hydrazide

HRID 1985018

반응식

HRID 1985018 반응식
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH2:9])=[O:7])=[CH:4][CH:3]=1.[CH2:12]([C:14]1[S:18][C:17]([CH:19]=O)=[CH:16][CH:15]=1)[CH3:13]>C(O)(=O)C.CCO>[CH2:12]([C:14]1[S:18][C:17]([CH:19]=[N:9][NH:8][C:6](=[O:7])[C:5]2[CH:10]=[CH:11][C:2]([OH:1])=[CH:3][CH:4]=2)=[CH:16][CH:15]=1)[CH3:13]

참가 물질

5

반응물 2

HCID 17424-Hydroxybenzoic acid hydrazideHCID 1698305-Ethyl-2-thiophenecarboxaldehyde

생성물 1

HCID 35953204-Hydroxy-benzoic acid (5-ethyl-thiophen-2-ylmethylene)-hydrazide수율 96.6%

시약·촉매·용매 2

HCID 176Acetic Acid촉매HCID 702Ethanol용매

실험 절차

To a solution of 4-hydroxy-benzoic acid hydrazide (0.3 g, 0.002 mol) and 5-ethyl-2-thiophenecarboxaldehyde (0.28 g, 0.002 mol) in abs. EtOH (10 mL), was added 1 drop of acetic acid. The reaction mixture was refluxed for 4 hours. The reaction mixture was cooling to room temperature and concentrated to remove solvent. The resulting residue was solidified by EtOAc to give white solid 0.53 g, in 96% yield, mp: 194.5° C. 1H NMR (CD3OD) δ 8.39 (s, 1H), 7.79 (d, 2H), 7.19 (s, 1H), 6.86 (d, 2H), 6.80 (s, 1H), 2.86 (q, 2H), 1.31 (t, 3H). 13C NMR (CDCl3) δ 166.5, 162.7, 153.1, 144.9, 137.7, 132.3, 130.8, 125.3, 124.8, 116.3, 24.7, 16.2. Anal. Calcd for C14H14N2O2S : C, 61.29; H, 5.14; N, 10.21. Found: C, 61.00; H, 5.18; N, 10.00.

후처리

  1. temperatureThe reaction mixture was refluxed for 4 hours
  2. concentrationconcentrated
  3. customto remove solvent

출처 및 근거

ORD 기록
ord-539847714a9f4bb2a1b25d18d7e24a23
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07544838B2

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