Nitromethane → (E)-2-(5-(3,4-dichlorophenyl)furan-2-yl)ethenamine

HRID 872447

반응식

HRID 872447 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[O:15][C:12]([CH:13]=O)=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[N+:16]([CH3:19])([O-])=O.C([O-])(=O)C.[NH4+]>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[O:15][C:12](/[CH:13]=[CH:19]/[NH2:16])=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

참가 물질

5

반응물 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 6176885-(3,4-Dichlorophenyl)-2-furaldehyde

생성물 1

HCID 67170044(E)-2-(5-(3,4-dichlorophenyl)furan-2-yl)ethenamine수율 92.5%

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
80 °C

실험 절차

To a stirred solution of 5-(3,4-dichlorophenyl)furfural (1.18 g, 4.89 mmol) in acetic acid (30 ml) was added nitromethane (0.535 ml, 9.78 mmol) and ammonium acetate (1.13 g, 14.7 mmol). The reaction mixture was heated at 80° C. for 4.5 h. Cooled reaction mixture was poured onto ice water (30 ml) and thus formed precipitate was filtered, washed with water and dried under vacuum to give 1.15 g (83%) of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 7.37 (d, 1H), 7.43 (d, 1H), 7.76 (d, 1H), 7.95 (dd, 1H), 8.03 (d, 1H), 8.19 (d, 1H), 8.31 (d, 1H).

후처리

  1. temperatureCooled
  2. customreaction mixture
  3. additionwas poured onto ice water (30 ml) and thus formed precipitate
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried under vacuum

출처 및 근거

ORD 기록
ord-d3ec8c8042a2450380a5863f5cd8d24d
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08975254B2

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