Phthalimide → N-[4-(2-Carbomethoxyphenyl)benzyl]phthalimide

HRID 1646921

反応式

HRID 1646921 の反応式
Br[CH:2]=[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH2:4]1.[C:19]1(=[O:29])[NH:23][C:22](=[O:24])[C:21]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:20]12.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:11]([C:10]1[CH:15]=[CH:16][CH:17]=[CH:18][C:9]=1[C:6]1[CH:7]=[CH:8][C:3]([CH2:2][N:23]2[C:22](=[O:24])[C:21]3=[CH:25][CH:26]=[CH:27][CH:28]=[C:20]3[C:19]2=[O:29])=[CH:4][CH:5]=1)([O:13][CH3:14])=[O:12]

参加物

5

反応物 3

HCID 6809PhthalimideHCID 11430Potassium CarbonateHCID 54201998Methyl 2-[4-(bromomethylene)phenyl]benzoate

生成物 1

HCID 19794415N-[4-(2-Carbomethoxyphenyl)benzyl]phthalimide収率 71%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

Methyl 2-[4-(bromomethylene)phenyl]benzoate (1.22 g, 0.04 mole), phthalimide (0.59 g, 0.04 mole), and potassium carbonate (0.55 g, 0.04 mole) are combined in 120 mL acetonitrile. The mixture is heated at reflux for 24 hours. At that time the mixture is filtered through celite and rotovapped to a residue. The residue is crystallized from ethyl acetate to afford 1.1 g (71% ) of the title compound as a tan solid mp 148°-150° C. 1H NMR (CDCl3) 7.9-7.1 (12H, m); 4.92 (2H, s); 3.63 (3H, s). Mass Spec. (DCI) m/z 372 (M+H). Analysis -calc'd for C23H17NO4.1/2 H2O: C, 72.62; H, 4.77: N, 3.68; found: C, 72.88; H, 4.55; N, 3.77.

後処理

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 24 hours
  3. filtrationAt that time the mixture is filtered through celite
  4. customThe residue is crystallized from ethyl acetate

出典と根拠

ORDレコード
ord-081acad0019a4f4080f0a0f1b1cba614
出典データセット
uspto-grants-1993_01
特許番号
US05182288

関連ノート

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