Water → HCID 86638789、化合物

HRID 1618882ノート

反応式

HRID 1618882 の反応式
[C:1]([C:3]1[C:4](=[C:18]([C:21]#[N:22])[C:19]#[N:20])[O:5][C:6]([CH3:17])([CH3:16])[C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]#[CH:15])=[CH:10][CH:9]=1)#[N:2].[N:23]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[N+:24]=[N-:25].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].O>C(O)C.S([O-])([O-])(=O)=O.[Cu+2]>[C:1]([C:3]1[C:4](=[C:18]([C:19]#[N:20])[C:21]#[N:22])[O:5][C:6]([CH3:17])([CH3:16])[C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:25]=[N:24][N:23]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH:15]=2)=[CH:10][CH:9]=1)#[N:2]

参加物

7

反応物 4

HCID 962WaterHCID 1390231-AzidooctaneHCID 23667548Sodium AscorbateHCID 86638786HCID 86638786、化合物

生成物 1

HCID 86638789HCID 86638789、化合物

試薬・触媒・溶媒 2

HCID 24462Copper Sulfate触媒HCID 702Ethanol溶媒

反応条件

温度
50 °C

実験手順

A mixture of 2-[3-cyano-4-(4-ethynyl-phenyl)-5,5-dimethyl-5H-furan-2-ylidene]malononitrile (90 mg, 0.34 mmol) and 1-azidooctane (80 mg, 0.51 mmol) in 15 mL ethanol was stirred at 50° C. under nitrogen and a solution of sodium ascorbate (25 mg, 0.12 mmol in 1 mL water) was added, followed by copper sulfate (15 mg, 0.06 mmol in 1 mL water) solution. The resulting mixture was stirred at the same temperature for 24 h, cooled and the reaction mixture was poured into cold water (100 mL). The mixture was stirred overnight at room temperature, the precipitate formed was filtered off and air dried. The crude product was recrystallized from dichloromethane/1-propanol, Yield: 70 mg (46%) Mp (DSc): 203° C.; IR (neat) 2933, 2974, 2266, 1574, 1565 cm−1, 1H NMR (400 MHz, CDCl3) δ 8.02 (d, J=8.4 Hz 2H), 7.87 (s, 1H), 7.85 (d, J=8.4 Hz, 2H), 4.39 (t, J=7.2 Hz, 2H), 1.94-1.96 (m, 2H), 1.82 (s, 6H), 1.20-1.31 (m, 10H), 0.82 (t, 3H); 13C NMR (CDCl3) δ 176.69, 175.14, 145.30, 136.33, 129.01, 126.40, 125.91, 121.03, 111.20, 110.47, 110.38, 100.79, 99.08, 59.85, 50.44, 31.41, 30.01, 29.41, 28.76, 28.66, 26.20, 22.31, 13.78; Anal. Calcd for C26H28N6O: C, 70.89; H, 6.41, N, 19.08. Found: C, 70.59, H, 6.18; N, 19.37. UV-Vis (CH2Cl2): λmax=384 nm ε=3.01×104 L.mol−1cm−1.

後処理

  1. stirringThe resulting mixture was stirred at the same temperature for 24 h
  2. temperaturecooled
  3. stirringThe mixture was stirred overnight at room temperature
  4. customthe precipitate formed
  5. filtrationwas filtered off
  6. customair dried
  7. customThe crude product was recrystallized from dichloromethane/1-propanol, Yield: 70 mg (46%) Mp (DSc)
  8. custom203° C.

出典と根拠

ORDレコード
ord-ec2366f758014660853c7ecb3df4f126
出典データセット
uspto-grants-2014_07
特許番号
US08772048B2

反応ノート

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