Phthalic Anhydride → 2-(2-(1H-Benzo[d]imidazol-2-yl)ethyl)isoindoline-1,3-dione

HRID 1610794노트

반응식

HRID 1610794 반응식
Cl.Cl.[NH2:3][CH2:4][CH2:5][C:6]1[NH:7][C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[N:10]=1.[C:15]1(=O)[O:20][C:18](=[O:19])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12.C(N(CC)CC)C>C(Cl)(Cl)Cl.C(OCC)(=O)C>[C:15]1(=[O:20])[N:3]([CH2:4][CH2:5][C:6]2[NH:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]=2)[C:18](=[O:19])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12

참가 물질

6

반응물 3

HCID 6811Phthalic AnhydrideHCID 8471TriethylamineHCID 27880712-(2-Aminoethyl)benzimidazole dihydrochloride

생성물 1

HCID 33521122-(2-(1H-Benzo[d]imidazol-2-yl)ethyl)isoindoline-1,3-dione수율 71.4%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 8857Ethyl Acetate용매

실험 절차

2-Aminoethylbenzimidazole dihydrochloride (Bull. Soc. Chim. Fr. 1991, 128, 255-259; 2.34 g, 10 mmol), phthalic anhydride (1.63 g, 11 mmol) and triethylamine (2.79 ml, 20 mmol) in chloroform (25 ml) were heated at reflux overnight, and the mixture was then cooled to room temperature, diluted with ethyl acetate and filtered off. The filtrate was washed with saturated sodium carbonate solution, buffer (pH=7) and saturated sodium chloride solution and dried over sodium sulphate. Chromatography (dichloromethane:methanol 10:1, Rf=0.4) gave 2.08 g of 2-(2-phthalimidylethyl)-benzimidazole (71.4% of theory) as a colourless foam. MS (DCI, NH3)=292 (M+H+). 1H-NMR (DMSO-d6): 3.15 (2H, t); 4.0 (2H, t); 7.05-7.2 (2H, m); 7.4-7.5 (2H, m); 7.8-7.9 (4H, m); 12.4 (1H, br s).

후처리

  1. temperatureat reflux overnight
  2. filtrationfiltered off
  3. washThe filtrate was washed with saturated sodium carbonate solution, buffer (pH=7) and saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate

출처 및 근거

ORD 기록
ord-c13ace95260645c7905fe54833e5850b
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06984642B1

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