A kind of method for one-pot synthesis of 1,2-diarylbenzimidazole and derivatives thereof
A benzimidazole and diaryl technology, applied in the field of synthesis 1, can solve the problems of long reaction time, strong acidity, high temperature, etc., and achieve the effects of simple operation, simple post-processing, and low economic cost
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Embodiment 1
[0024] This embodiment is the synthesis of 1,2-diphenyl-1H-benzimidazole, with o-phenylenediamine, benzaldehyde, and iodobenzene as raw materials, and its reaction formula is as follows:
[0025]
[0026] Preparation method: Take 1mmol o-phenylenediamine, 1.2mmol benzaldehyde, and 1mmol iodobenzene as raw materials, put them into a 50mL pressure-resistant tube, and use 20mol% Fe 2 o 3 As a catalyst, 2mmol KOH was used as a base, the amount of 1,10-phenanthroline was 20mol%, the amount of N,N-dimethylformamide was 5mL, the temperature was 120°C, and the reaction was stirred for 24h.
[0027] The reaction solution was filtered by suction, distilled under reduced pressure, and passed through a column to obtain a white solid.
[0028] Yield 61%, 1,2-diphenyl-1H-benzimidazole is a white solid; 1 H NMR (400MHz, CDCl 3 ): δ=7.26-7.29(m, 2H), 7.31-7.36(m, 6H), 7.45-7.52(m, 3H), 7.56(d, J=7.2Hz, 2H), 7.89(d, J=8.0 Hz, 1H).
[0029] ESI-MS m / z: 271.3 ([M+H]+).
Embodiment 2
[0031] This embodiment is the synthesis of 1,2-diphenyl-1H-benzimidazole, with o-phenylenediamine, benzaldehyde, and iodobenzene as raw materials, and its reaction formula is as follows:
[0032]
[0033] Preparation method: Take 1mmol o-phenylenediamine, 1.2mmol benzaldehyde, and 1mmol iodobenzene as raw materials, put them into a 50mL pressure-resistant tube, and use 20mol% FeCl 3 As a catalyst, 2mmol NaOH was used as a base, the amount of 8-hydroxyquinoline was 20mol%, the amount of dimethyl sulfoxide was 5mL, the temperature was 130°C, and the reaction was stirred for 24h.
[0034] The reaction solution was filtered by suction, distilled under reduced pressure, and passed through a column to obtain a white solid.
[0035] Yield 52%, 1,2-diphenyl-1H-benzimidazole is a white solid; 1 H NMR (400MHz, CDCl 3 ): δ=7.26-7.29(m, 2H), 7.31-7.36(m, 6H), 7.45-7.52(m, 3H), 7.56(d, J=7.2Hz, 2H), 7.89(d, J=8.0 Hz, 1H).
[0036] ESI-MS m / z: 271.3 ([M+H]+).
Embodiment 3
[0038] This embodiment is the synthesis of 1,2-diphenyl-1H-benzimidazole, with o-phenylenediamine, benzaldehyde, and iodobenzene as raw materials, and its reaction formula is as follows:
[0039]
[0040] Preparation method: Take 1mmol o-phenylenediamine, 1.2mmol benzaldehyde, and 1mmol iodobenzene as raw materials, put them into a 50mL pressure-resistant tube, use 20mol% Fe as a catalyst, and 2mmol KO t Bu was used as a base, the amount of L-proline was 20 mol%, the amount of N,N-dimethylformamide was 5 mL, the temperature was 130°C, and the reaction was stirred for 24 hours.
[0041] The reaction solution was filtered by suction, distilled under reduced pressure, and passed through a column to obtain a white solid.
[0042] Yield 43%, 1,2-diphenyl-1H-benzimidazole is a white solid; 1 H NMR (400MHz, CDCl 3 ): δ=7.26-7.29(m, 2H), 7.31-7.36(m, 6H), 7.45-7.52(m, 3H), 7.56(d, J=7.2Hz, 2H), 7.89(d, J=8.0 Hz, 1H).
[0043] ESI-MS m / z: 271.3 ([M+H]+).
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