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

HRID 1646921

반응식

HRID 1646921 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-081acad0019a4f4080f0a0f1b1cba614
출처 데이터셋
uspto-grants-1993_01
특허 번호
US05182288

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