Dimethylformamide → 4-ethenyl-5-[4-(4-methoxyphenyl)piperazin-1-yl]-2,2,6,7-tetramethyl-1-benzofuran-3(2H)-one

HRID 2063789ノート

反応式

HRID 2063789 の反応式
Br[CH2:2][CH2:3][N:4]([CH2:13][CH2:14]Br)[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1.C(=O)([O-])O.[Na+].CN(C=O)C.[NH2:26][C:27]1[C:28]([CH3:42])=[C:29]([CH3:41])[C:30]2[O:34][C:33]([CH3:36])([CH3:35])[C:32](=[O:37])[C:31]=2[C:38]=1[CH:39]=[CH2:40]>C(OCC)(=O)C.O>[CH:39]([C:38]1[C:31]2[C:32](=[O:37])[C:33]([CH3:35])([CH3:36])[O:34][C:30]=2[C:29]([CH3:41])=[C:28]([CH3:42])[C:27]=1[N:26]1[CH2:14][CH2:13][N:4]([C:5]2[CH:6]=[CH:7][C:8]([O:11][CH3:12])=[CH:9][CH:10]=2)[CH2:3][CH2:2]1)=[CH2:40]

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 667591945-amino-4-ethenyl-2,2,6,7-tetramethyl-1-benzofuran-3(2H)-oneHCID 66759772N,N-bis(2-bromoethyl)-4-methoxyaniline

生成物 1

HCID 667602304-ethenyl-5-[4-(4-methoxyphenyl)piperazin-1-yl]-2,2,6,7-tetramethyl-1-benzofuran-3(2H)-one収率 8.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

N,N-bis(2-bromoethyl)-4-methoxyaniline (2.45 g, 7.63 mmol) and sodium hydrogencarbonate (1.25 g, 1.40 mmol) were added to a solution of DMF (36 mL) containing 5-amino-4-ethenyl-2,2,6,7-tetramethyl-1-benzofuran-3(2H)-one (1.47 g, 6.36 mmol) synthesized in Reference Example 22, and the mixture was stirred at 120° C. for 16 hours. After cooled to room temperature, water was added to the mixture, and extraction was performed using ethyl acetate. It was dried using anhydrous magnesium sulfate. After that, the solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate: 100:0 to 90:10) to give 217 mg of the title compound (yield: 8%).

後処理

  1. customsynthesized in Reference Example 22
  2. temperatureAfter cooled to room temperature
  3. customIt was dried
  4. customAfter that, the solvent was removed under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate: 100:0 to 90:10)

出典と根拠

ORDレコード
ord-0fb8c894e81d4c269bda570e6e8ec3ea
出典データセット
uspto-grants-2012_10
特許番号
US08288390B2

反応ノート

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