Ammonium Chloride → 3-Cyano-5-[6-(N,N-diethylamino)benzo[b]furanylmethylene]-4-phenyl-2-furanone

HRID 1199489노트

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HRID 1199489 반응식
[CH2:1]([N:3]([C:6]1[CH:7]=[CH:8][C:9]2[CH:13]=[C:12]([CH:14]=O)[O:11][C:10]=2[CH:16]=1)[CH2:4][CH3:5])[CH3:2].[C:17]([CH:19]1[C:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:22][O:21][C:20]1=[O:30])#[N:18].[NH4+].[Cl-]>N1C=CC=CC=1>[C:17]([C:19]1[C:20](=[O:30])[O:21][C:22](=[CH:14][C:12]2[O:11][C:10]3[CH:16]=[C:6]([N:3]([CH2:1][CH3:2])[CH2:4][CH3:5])[CH:7]=[CH:8][C:9]=3[CH:13]=2)[C:23]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)#[N:18]

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 147167106-(Diethylamino)-2-benzofurancarboxaldehydeHCID 151652113-Cyano-4-phenyl-2-furanone

생성물 1

HCID 703589443-Cyano-5-[6-(N,N-diethylamino)benzo[b]furanylmethylene]-4-phenyl-2-furanone

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
80 °C

실험 절차

To 5 mL of pyridine in a 15 mL round-bottom flask was added 217 mg (1 mmol) of the compound of Example 2 and 172 mg (1 mmol) of 3-cyano-4-phenyl-2-furanone. The solution was heated at 80° C. for one hour, colled and poured into 20 mL dilute NH4Cl. The resulting mixture was extracted 2X with 20 mL 3:2 hexanes Et2O and the combined organic extracts were washed once with 10 mL of water, The organic phase was dried (MgSO4) and the solvent removed by rotary evaporation. The resulting solid was purified by flash chromatography (7:2 cyclohexane/EtOAc; SiO2, 1 ×12") to yield 292 mg of dye. Anal. calcd. for C24H20N2O3 : C, 74.2; H, 5.4; N, 7.5. Found: C, 74.0; H, 5.2; N, 6.9.

후처리

  1. extractionThe resulting mixture was extracted 2X with 20 mL 3:2 hexanes Et2O
  2. washthe combined organic extracts were washed once with 10 mL of water
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customthe solvent removed by rotary evaporation
  5. customThe resulting solid was purified by flash chromatography (7:2 cyclohexane/EtOAc; SiO2, 1 ×12")
  6. customto yield 292 mg of dye

출처 및 근거

ORD 기록
ord-aa19847629fd435c9788e278cc58e8a5
출처 데이터셋
uspto-grants-1990_02
특허 번호
US04900831

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