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

HRID 1610794Notes

Reaction equation

HRID 1610794 reaction equation
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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-c13ace95260645c7905fe54833e5850b
Source dataset
uspto-grants-2006_01
Patent number
US06984642B1

Reaction notes

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