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[ CAS No. 43181-78-8 ] {[proInfo.proName]}

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Product Details of [ 43181-78-8 ]

CAS No. :43181-78-8 MDL No. :MFCD00193102
Formula : C14H11ClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :PVLIRTAXXPPHCJ-UHFFFAOYSA-N
M.W : 242.70 Pubchem ID :3821987
Synonyms :

Safety of [ 43181-78-8 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 43181-78-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 43181-78-8 ]

[ 43181-78-8 ] Synthesis Path-Downstream   1~75

  • 1
  • [ 109-01-3 ]
  • [ 43181-78-8 ]
  • [ 57897-96-8 ]
  • 3
  • [ 4857-06-1 ]
  • [ 100-39-0 ]
  • [ 43181-78-8 ]
YieldReaction ConditionsOperation in experiment
97% General procedure: 2-Chloro-1H-benzoimidazole (3.04 g, 20 mmol) was dissolved in dry DMF (15 mL) at 0 C, to the solution was added NaH (0.91 g, 22.7 mmol), and the mixture was stirred for 1 h at 0 C, then halide (21.6 mmol) was added. The mixture was stirred overnight at room temperature and was poured into water (50 mL) and stirred for 1 h, filtrated, washed with water and dried to afford 4a-d.
88% In a round bottom flask fitted with amagnetic stirrer, 2-chloro-1H-benzimidazole, 3, (0.50 g, 3.3 mmol) was dissolved in DMSO (3mL) and then NaH (60%; 0.19 g, 4.9 mmol) was added at 0 C and stirred for 1h. Next, benzylbromide (0.67 g, 3.9 mmol) was added to the suspension and the reaction was stirred at rt for 12h. Ice-cold water (15 mL) was added to the mixture and resulting precipitate was collected viafiltration. The filtrate was washed with water and dried under vacuum to give desired product, 4,as a white solid (0.75 g, 88%). LCMS: RT = 2.69 min., >98% 215 and 254 nm, m/z = 243.0 [M+ H]+. 1H NMR (499 MHz, CDCl3) δ 7.68 (d, J = 7.4 Hz, 1H), 7.35 - 7.24 (m, 5H), 7.16 (d, J =6.8 Hz, 2H), 5.38 (s, 2H). 13C NMR (126 MHz, CDCl3) δ 141.33, 134.83, 128.99, 128.22, 126.76,123.53, 123.05, 119.18, 109.98, 47.94.
85% Step 1: 1.00 g, 6.5 mmol of 2-chlorobenzimidazole, dissolved in 15 mL of tetrahydrofuran, added 174 mg, 12.1 mmol of 60% sodium hydride, stirred for half an hour, then added 1.2 mL, 10.1 mmol of benzyl bromide, and the mixture was stirred at room temperature. After 2 hours, water was added, ethyl acetate was extracted, washed with water, saturated with brine, dried, concentrated, and then purified by column chromatography to give 1-benzyl-2-chlorobenzimidazole, 1.34 g of pale yellow liquid. The rate is 85%.
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 110℃; for 12h; General procedure: Alternatively, to a stirred mixture of 2-chlorobenzimidazole (1.0 eq.) and R3CH2Br (1.0 eq.) in dimethylformamide was added N,N-diisopropylethylamine (1.5 eq.). The reaction mixture was heated to 110 C and stirred for 12 h. After the reaction was completed, the reaction mixture was cooled down to room temperature, diluted with ethyl acetate and washed with water. The organic layer was dried over anhydrous MgSO4 and concentrated in vacuo. The crude product was purified by flash column chromatography (ethyl acetate/hexane) to give desired product 1d.
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 110℃; for 12h; General procedure: To a stirred solution of 1c (1.0 eq.) and POCl3 (10 eq.) was addeda few drops of conc. HCl. The reaction mixture was heated to 150 C and stirred for 3 h. After the reaction was completed, the reaction mixture was poured into ice water, neutralized with 1 N aq. NaOH and extracted with ethyl acetate. The organic layer was washed with water, dried over Na2SO4 and concentrated in vacuo to givecrude product 1d. Alternatively, to a stirred mixture of 2-chlorobenzimidazole (1.0 eq.) and R3CH2Br (1.0 eq.) in dimethylformamide was added N,N-diisopropylethylamine (1.5 eq.). The reaction mixture was heated to 110 C and stirred for 12 h. After the reaction was completed, the reaction mixture was cooled down to room temperature, diluted with ethyl acetate and washed with water. The organic layer was dried over anhydrous MgSO4 and concentrated in vacuo. The crude product was purified by flash column chromatography (ethyl acetate/hexane) to give desired product 1d.

  • 4
  • [ 841-77-0 ]
  • [ 43181-78-8 ]
  • 1-benzyl-2-<4-(diphenylmethyl)piperazin-1-yl>-1H-benzimidazole [ No CAS ]
  • 6
  • [ 109-73-9 ]
  • [ 43181-78-8 ]
  • 1-benzyl-N-butyl-1H-benzo[d]imidazol-2-amine [ No CAS ]
  • 9
  • [ 43181-78-8 ]
  • hydroxylamine [ No CAS ]
  • 1-benzyl-2-hydroxyaminobenzimidazole [ No CAS ]
  • 10
  • [ 43181-78-8 ]
  • [ 156642-03-4 ]
  • [ 250342-76-8 ]
  • 11
  • [ 4857-06-1 ]
  • PhCH2X [ No CAS ]
  • [ 43181-78-8 ]
  • 12
  • [ 217096-06-5 ]
  • tert-butyl carboxylate [ No CAS ]
  • [ 664340-59-4 ]
  • [ 43181-78-8 ]
  • [ 77279-24-4 ]
  • [ 664340-25-4 ]
YieldReaction ConditionsOperation in experiment
85% With hydrogenchloride; potassium carbonate;palladium-carbon; In ethanol; chloroform; N,N-dimethyl-formamide; acetonitrile; Example 153 Preparation of 2-[4-[2-(benzimidazol-2-yloxy)ethyl]piperazin-1-yl]-N-[2,4-bis(methylthio)-6-methyl-3-pyridyl]acetamide: To a solution of tert-butyl 4-(2-hydroxyethyl)-1-piperazinecarboxylate (230 mg, 1.00 mmol) in DMF (2 ml) was added sodium hydride (55%, 52 mg, 1.19 mmol) with ice-cooling and stirred at 75 C. for 30 minutes, and then added 1-benzyl-2-chlorobenzimidazole (243 mg, 1.00 mmol) and stirred at 75 C. for 24 hours. The reaction solution was concentrated in vacuo, and the resulting residue was dissolved in chloroform. The organic layer was washed with water and a saturated sodium chloride solution successively, dried over anhydrous sodium sulfate and concentrated in vacuo. The resulting residue was purified by a silica gel column chromatography (silica gel 25 g, developing solvent; hexane:ethyl acetate=5:1 1:1) to provide 369 mg (yield 85%) of tert-butyl [4-[2-(benzimidazol-2-yloxy)ethyl]piperazin-1-yl]carboxylate as colorless solid. To a solution of this tert-butyl carboxylate (326 mg, 0.747 mmol) in ethanol (10 ml) were added conc. hydrochloric acid (0.5 ml, 16.3 mmol) and 10% palladium carbon catalyst (328 mg), and stirred under hydrogen atmosphere at 55 C. for 17 hours. The reaction solution was filtered through celite, and the filtrate was concentrated in vacuo. The resulting residue was purified by a silica gel preparative thin layer chromatography (developing solvent; chloroform:sat. ammonia methanol=10:1) to provide 121 mg (yield 66%) of 1-[2-(benzimidazol-2-yloxy)ethyl]piperazine as colorless amorphous. To a solution of this piperazine compound (119 mg, 0.483 mmol) in acetonitrile (2 ml) were added 2-bromo-N-[2,4-bis(methylthio)-6-methylpyridin-3-yl]acetamide (156 mg, 0.486 mmol) and potassium carbonate (80 mg, 0.579 mmol) successively with ice-cooling, and stirred at room temperature for 20 hours. The reaction solution was diluted with water and extracted with chloroform. The organic layer was washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo. The resulting residue was purified by a silica gel preparative thin layer chromatography (developing solvent; chloroform:sat. ammonia methanol=10:1) to provide 145 mg (yield 62%) of the desired compound as colorless oil. IR (neat) cm-1: 3260, 1683, 1630, 1558, 1486. 1H-NMR (CDCl3) delta: 2.39 (3H, s), 2.48 (3H, s), 2.51 (3H, s), 2.65-2.85 (8H, m), 2.89 (2H, t, J=5.4 Hz), 3.21 (2H, s), 4.65 (2H, t, J=5.4 Hz), 6.63 (2H, s), 7.09-7.15 (2H, m), 7.31-7.38 (1H, m), 8.54 (1H, br s).
  • 13
  • [ 43181-78-8 ]
  • 4'-(1-benzyl-1<i>H</i>-benzoimidazol-2-yl)-biphenyl-4-ol [ No CAS ]
  • 14
  • [ 43181-78-8 ]
  • 2-[4'-(1-benzyl-1<i>H</i>-benzoimidazol-2-yl)-biphenyl-4-yloxy]-3-phenyl-propionic acid methyl ester [ No CAS ]
  • 15
  • [ 43181-78-8 ]
  • 2-[4'-(1-benzyl-1<i>H</i>-benzoimidazol-2-yl)-biphenyl-4-yloxy]-3-phenyl-propionic acid [ No CAS ]
  • 16
  • [ 43181-78-8 ]
  • [ 51314-51-3 ]
  • 17
  • [ 615-16-7 ]
  • [ 43181-78-8 ]
  • 18
  • [ 4857-06-1 ]
  • sodium hydride-mineral oil [ No CAS ]
  • [ 100-39-0 ]
  • [ 43181-78-8 ]
YieldReaction ConditionsOperation in experiment
110 g (93%) In N-methyl-acetamide; water; N,N-dimethyl-formamide; A. 1-Benzyl-2-chlorobenzimidazole A solution of 2-chlorobenzimidazole (100 g, 0.65 mol) in 500 ml of dimethylformamide (DMF) was added dropwise to a stirred suspension of 60% sodium hydride-mineral oil dispersion (28 g, 0.70 mol) in 500 ml of DMF. Mild intermittent cooling was required. After the addition was completed the mixture was stirred an additional 15 min and benzylbromide (82.6 g, 0.49 mol) was added dropwise with mild intermittent cooling. The reaction mixture was stirred an additional 1.5 h and 1 L of water was added. The mixture was extracted with benzene. The extract was dried (Na2 SO4), concentrated and the residue crystallized from isopropyl ether to obtain 110 g (93%), mp 102-105 C.
  • 19
  • [ 41838-46-4 ]
  • [ 43181-78-8 ]
  • [ 75971-14-1 ]
YieldReaction ConditionsOperation in experiment
2.0 g (18%) With sodium hydroxide; EXAMPLE 4 N-(1-Methyl-4-piperidinyl)-1-(phenylmethyl)-1H-benzimidazol-2-amine A mixture of 18 g (0.157 mol) of 4-amino-1-methylpiperidine and 7.5 g (0.0315 mol) of 2-chloro-1-(phenylmethyl)-1H-benzimidazole was heated to 130 C. for 24 hours (oil bath). Sodium hydroxide solution (150 ml, 2.5N) was added to the reaction mixture which was then extracted with 2*200 mL of CH2 Cl2. The combined organic extracts were washed with 150 mL of H2 O, dried over Na2 SO4, filtered and concentrated by rotary evaporation. The residue was subjected to high vacuum at 60 C. for two hours, and the resulting residue crystallized from acetone/H2 O. The resulting crystals were recrystallized from toluene and a trace of water to give 2.0 g (18%) of white analytically pure crystals as the dihydrate, mp 94-102 C. Analysis: Calculated for C20 H24 N4.2H2 O: C, 67.39; H, 7.92; N, 15.72. Found: C, 67.22; H, 7.85; N, 15.67.
  • 20
  • [ 110-85-0 ]
  • [ 43181-78-8 ]
  • 1,4-Bis(1-benzylbenzimidazol-2-yl)piperazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; Example 15 1,4-Bis(1-benzylbenzimidazol-2-yl)piperazine (Compound 5c): A mixture of <strong>[43181-78-8]1-benzyl-2-chlorobenzimidazole</strong> (1.21 g, 5.0 mmol), piperazine (0.22 g, 2.5 mmol) and potassium carbonate (0.69 g, 5.0 mmol) in DMF (10 ml) was heated to reflux for three days. The cooled mixture was poured into ice-water. The precipitate was filtered off and washed with refluxing ethyl acetate to leave 5c. Yield: 0.46 g. M.p. 247-248 C.
  • 21
  • [ 43181-78-8 ]
  • [ 14180-45-1 ]
  • 22
  • [ 1228423-32-2 ]
  • [ 43181-78-8 ]
  • C34H27N5O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium tert-butylate;tris-(dibenzylideneacetone)dipalladium(0); DavePhos; In toluene; at 108℃; for 24h;Inert atmosphere; Example 46; (1-Aminomethyl-6,8-dimethoxy-isoquinolin-4-yl)-(1-benzyl-1H-benzoimidazol-2-yl)-amine; 1-Benzyl-2-chlorobenzimidazole (51 mg, 0.21 mmol), Example 45C (76 mg, 0.21 mmol), 2-dicyclohexylphosphino-2'-(N,N-dimethyl-amino)biphenyl (17 mg, 0.1 mmol), tris(dibenzylideneacetone)dipalladium(0) (10 mg, 0.011 mmol), and potassium tert-butoxide (24 mg, 0.21 mmol) were combined in toluene (5 mL) in a flask purged with nitrogen. The reaction was stirred at 108 C. for 24 h. Solvent was removed in vacuo, and the residue was deprotected by stirring with hydrazine (0.1 mL) in ethanol (4 mL) for 1 h. Purification by Prep-HPLC gave 5.6 mg (5%) of the title compound (TFA salt) as an off-white solid. H1-NMR (MeOD-d4): δ 8.59 (s, 1H), 7.56 (d, 1H, J=6.8 Hz), 7.32-7.46 (m, 9H), 6.87 (s, 1H), 6.69 (s, 1H), 5.73 (s, 2H), 4.92 (s, 2H), 4.06 (s, 3H), 3.72 (s, 3H). MS (ES) (M+H) calc'd for C26H25N5O2, 440; found 440.
  • 23
  • [ 773837-37-9 ]
  • [ 43181-78-8 ]
  • 1-benzyl-2-cyano-1H-benzoimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% In N,N-dimethyl-formamide; at 100℃; for 2h; General procedure: 4 (8.7 mmol) was dissolved in dry DMF (15 mL), to the solution was added NaCN (9.2 mol), and the mixture was stirred for 2 h at 100 C. The mixture was poured into water (50 mL), filtrated, washed with water and dried to afford 5.
  • 24
  • [ 1331868-37-1 ]
  • [ 43181-78-8 ]
  • [ 1331868-32-6 ]
  • 25
  • [ 1393082-68-2 ]
  • [ 43181-78-8 ]
  • [ 1393082-69-3 ]
  • 26
  • [ 1131-18-6 ]
  • [ 43181-78-8 ]
  • [ 882236-02-4 ]
  • 27
  • [ 43181-78-8 ]
  • [ 920939-74-8 ]
  • 28
  • [ 43181-78-8 ]
  • [ 554424-57-6 ]
  • 29
  • [ 43181-78-8 ]
  • [ 731004-38-9 ]
  • 30
  • [ 43181-78-8 ]
  • [ 31493-51-3 ]
YieldReaction ConditionsOperation in experiment
With thiourea;Sealed tube; Microwave irradiation; General procedure: A mixture of 4a-c (10 mM) and thiourea (0.76 g, 10 mM) was taken in a 10 mL CEM-reaction tube sealed by rubber stopper and subjected to microwave irradiation for 2 min at 130 C in a commercial microvawe reactor. After that, the tube was cooled and the completion of reaction was checked by TLC. Then the reaction mixture was poured into ice-cold water (50 mL). The separated solid was filtered, washed with water (2 x 10 mL) and dried. Yields are shown in Table I. The crude products were purified by recrystallization from ethyl acetate to obtain pure 5a-c, identical with the same products obtained above.
  • 31
  • [ 43181-78-8 ]
  • [ 52986-15-9 ]
YieldReaction ConditionsOperation in experiment
91% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; d8-isopropanol; potassium carbonate; bis(dibenzylideneacetone)-palladium(0); In acetonitrile; at 100℃; for 2.5h;Inert atmosphere; Microwave irradiation; General procedure: In a dried microwave reactor vessel were added 3-bromoquinoline(0.204 mL, 1.5 mmol), Pd(dba)2 (86 mg, 0.15 mmol), K2CO3carbonate (415 mg, 3.00 mmol), S-Phos (185 mg, 0.45 mmol), dryD8-IPA (0.500 mL) and MeCN (1 mL). The mixture was degassedand placed under a nitrogen atmosphere. The sealed reaction tubewas heated to 100 C in a microwave (Biotage Initiator) for 2.5 h.The solvents were removed under reduced pressure, the crudematerial pre-loaded on to silica and purified using flash silica chromatography(15% EtOAc/heptane). The fractions containing thedesired compound were combined and evaporated to dryness toafford 3-deuterioquinoline (140 mg, 72%); 1H NMR (400 MHz,DMSO, 27 C): d (ppm) 7.62 (ddd, J = 1.20, 6.89, 8.11 Hz, 1H), 7.77(ddd, J = 1.50, 6.87, 8.43 Hz, 1H), 7.99 (dd, J = 1.33, 8.18 Hz, 1H),8.03 (d, J = 8.41 Hz, 1H), 8.37 (s, 1H), 8.91 (d, J = 1.70 Hz, 1H); 13CNMR (176 MHz, DMSO, 30 C) 121.0, 126.4, 127.8, 128.0, 128.8,129.3, 135.8, 147.7, 150.3; HRMS (EI): M+, found 130.0643,C9H6DN requires 130.0641.
  • 32
  • [ 5822-13-9 ]
  • [ 43181-78-8 ]
  • 33
  • [ 28643-53-0 ]
  • [ 43181-78-8 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; trichlorophosphate; In water; at 150℃; for 3h; General procedure: To a stirred solution of 1c (1.0 eq.) and POCl3 (10 eq.) was added a few drops of conc. HCl. The reaction mixture was heated to 150 C and stirred for 3 h. After the reaction was completed, the reaction mixture was poured into ice water, neutralized with 1 N aq. NaOH and extracted with ethyl acetate. The organic layer was washed with water, dried over Na2SO4 and concentrated in vacuo to give crude product 1d.
With hydrogenchloride; trichlorophosphate; In water; at 150℃; for 3h; General procedure: To a stirred solution of 1c (1.0 eq.) and POCl3 (10 eq.) was addeda few drops of conc. HCl. The reaction mixture was heated to 150 C and stirred for 3 h. After the reaction was completed, the reaction mixture was poured into ice water, neutralized with 1 N aq. NaOH and extracted with ethyl acetate. The organic layer was washed with water, dried over Na2SO4 and concentrated in vacuo to givecrude product 1d. Alternatively, to a stirred mixture of 2-chlorobenzimidazole (1.0 eq.) and R3CH2Br (1.0 eq.) in dimethylformamide was added N,N-diisopropylethylamine (1.5 eq.). The reaction mixture was heated to 110 C and stirred for 12 h. After the reaction was completed, the reaction mixture was cooled down to room temperature, diluted with ethyl acetate and washed with water. The organic layer was dried over anhydrous MgSO4 and concentrated in vacuo. The crude product was purified by flash column chromatography (ethyl acetate/hexane) to give desired product 1d.
  • 34
  • [ 43181-78-8 ]
  • [ 111678-96-7 ]
  • 35
  • [ 43181-78-8 ]
  • [ 24134-56-3 ]
  • 36
  • [ 141-43-5 ]
  • [ 43181-78-8 ]
  • [ 86978-99-6 ]
YieldReaction ConditionsOperation in experiment
at 150℃; for 0.5h;Microwave irradiation; General procedure: A mixture of 1d (1.0 eq.) and ethanolamine (10 eq.) was heated to 150 C for 30 min by use of microwave irradiation. After the reaction was completed, the reaction mixture was cooled down to room temperature. The precipitated solid was filtered and washed with diethyl ether. The crude product was purified by flash column chromatography (MeOH/methylene chloride) to give desired product 1e.
at 150℃; for 0.5h;Microwave irradiation; General procedure: A mixture of 1d (1.0 eq.) and ethanolamine (10 eq.) was heated to 150 C for 30 min by use of microwave irradiation. After the reaction was completed, the reaction mixture was cooled down to room temperature. The precipitated solid was filtered and washed with diethyl ether. The crude product was purified by flash column chromatography (MeOH/methylene chloride) to give desired product 1e.
  • 37
  • [ 100-39-0 ]
  • [ 43181-78-8 ]
  • 39
  • [ 5729-06-6 ]
  • [ 43181-78-8 ]
  • 40
  • [ 43181-78-8 ]
  • 2-((1-benzyl-1H-benzimidazol-2-yl)thio)acetonitrile [ No CAS ]
  • 42
  • C25H26FeNP [ No CAS ]
  • [ 43181-78-8 ]
  • C39H36FeN3P [ No CAS ]
  • 43
  • [ 43182-10-1 ]
  • [ 43181-78-8 ]
  • 44
  • 3-(4-(mercaptomethyl)-1-phenyl-1H-pyrazol-3-yl)-2H-chromen-2-one [ No CAS ]
  • [ 43181-78-8 ]
  • 3-(4-(((1-benzyl-1H-benzo[d]imidazol-2-yl)thio)methyl)-1-phenyl-1H-pyrazol-3-yl)-2H-chromen-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With tetrabutylammomium bromide; potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 4.5h; General procedure: A mixture of 10 (5 mM), 14 (5 mM) in DMF (20 mL) containing K2CO3 (2 mM) and TBAB (2 mM) was stirred at RT for a period of 3-5 h. The reaction was monitored by TLC analysis. After the completion of reaction, the mixture was poured into ice-cold water (30 mL). The separated solid was filtered, washed with water (2 9 10 mL) and dried. The crude product was recrystallized from ethanol to yield pure 13.
  • 45
  • [ 43181-78-8 ]
  • [ 388072-09-1 ]
  • C20H19N3O [ No CAS ]
  • 46
  • [ 847644-09-1 ]
  • [ 43181-78-8 ]
  • 1-benzyl-N-(oxazol-5-ylmethyl)-1H-benzo[d]imidazol-2-amine [ No CAS ]
  • 47
  • oxazol-2-yl-methylamine [ No CAS ]
  • [ 43181-78-8 ]
  • 1-benzyl-N-(oxazol-2-ylmethyl)-1H-benzo[d]imidazol-2-amine [ No CAS ]
  • 48
  • [ 55661-33-1 ]
  • [ 43181-78-8 ]
  • 1-benzyl-N-(thiazol-2-ylmethyl)-1H-benzo[d]imidazol-2-amine [ No CAS ]
  • 49
  • [ 22095-34-7 ]
  • [ 43181-78-8 ]
  • 1-benzyl-N-(1-(furan-2-yl)ethyl)-1H-benzo[d]imidazol-2-amine [ No CAS ]
  • 50
  • [ 617-89-0 ]
  • [ 43181-78-8 ]
  • 1-benzyl-N-(furan-2-ylmethyl)-1H-benzo[d]imidazol-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% at 200℃; for 0.5h;Microwave irradiation; A 10 mL microwavevial with stir bar was charged with <strong>[43181-78-8]1-benzyl-2-chloro-1H-benzo[d]imidazole</strong>, 4, (50 mg, 0.20mmol) and furfuryl amine (0.20 g, 2.0 mmol). The mixture was subjected to microwave irradiationat 200 C for 30 min. The mixture was diluted with ethyl acetate (50 mL) and washed with water(25 mL) and brine (25 mL). The organic layer was dried (Na2SO4), evaporated and purified byreverse phase chromatography (0-100% water/ACN). Fractions collected were evaporated to yielddesired product, 2 (30 mg, 48%). LCMS: RT = 2.07 min., >98% 215 and 254 nm, m/z = 304.1[M + H]+. 1H NMR (499 MHz, CDCl3) δ 7.58 (d, J = 7.8 Hz, 1H), 7.34 (m, 4H), 7.17 (t, J = 9.2Hz, 3H), 7.13 - 7.05 (m, 2H), 6.31 (s, 1H), 6.23 (s, 1H), 5.13 (s, 2H), 4.71 (d, J = 5.4 Hz, 2H),4.34 (s, 1H). 13C NMR (126 MHz, CDCl3) δ 153.76, 151.70, 142.14, 135.29, 134.88, 129.19,128.14, 126.43, 121.56, 120.03, 116.85, 110.40, 107.46, 107.41, 45.72, 40.51.
  • 51
  • [ 3731-51-9 ]
  • [ 43181-78-8 ]
  • 1-benzyl-N-(pyridin-2-ylmethyl)-1H-benzo[d]imidazol-2-amine [ No CAS ]
  • 52
  • [ 27757-85-3 ]
  • [ 43181-78-8 ]
  • C19H17N3S [ No CAS ]
  • 53
  • [ 609-38-1 ]
  • [ 43181-78-8 ]
  • C19H15N3O2 [ No CAS ]
  • 54
  • [ 4753-75-7 ]
  • [ 43181-78-8 ]
  • C20H19N3O [ No CAS ]
  • 55
  • [ 43181-78-8 ]
  • [ 100-46-9 ]
  • [ 27185-23-5 ]
  • 56
  • [ 62-53-3 ]
  • [ 43181-78-8 ]
  • [ 24068-33-5 ]
  • 57
  • [ 462-08-8 ]
  • [ 43181-78-8 ]
  • 1-benzyl-N-(pyridin-3-yl)-1H-benzo[d]imidazol-2-amine [ No CAS ]
  • 58
  • [ 3731-52-0 ]
  • [ 43181-78-8 ]
  • 1-benzyl-N-(pyridin-3-ylmethyl)-1H-benzo[d]imidazol-2-amine [ No CAS ]
  • 59
  • [ 3731-53-1 ]
  • [ 43181-78-8 ]
  • 1-benzyl-N-(pyridin-4-ylmethyl)-1H-benzo[d]imidazol-2-amine [ No CAS ]
  • 60
  • [ 43181-78-8 ]
  • [ 74-89-5 ]
  • [ 43181-77-7 ]
  • 61
  • [ 43181-78-8 ]
  • [ 432047-36-4 ]
  • 1-benzyl-N-(1-(thiazol-2-yl)ethyl)-1H-benzo[d]imidazol-2-amine [ No CAS ]
  • 62
  • [ 37798-05-3 ]
  • [ 43181-78-8 ]
  • N-(benzofuran-2-ylmethyl)-1-benzyl-1H-benzo[d]imidazol-2-amine [ No CAS ]
  • 63
  • (5-methyl-1,3,4-thiadiazol-2-yl)methanamine [ No CAS ]
  • [ 43181-78-8 ]
  • 1-benzyl-N-((5-methyl-1,3,4-thiadiazol-2-yl)methyl)-1H-benzo[d]imidazol-2-amine [ No CAS ]
  • 64
  • [ 43181-78-8 ]
  • (5-methyl-1,2,4-oxadiazol-3-yl)methylamine [ No CAS ]
  • 1-benzyl-N-((5-methyl-1,2,4-oxadiazol-3-yl)methyl)-1H-benzo[d]imidazol-2-amine [ No CAS ]
  • 65
  • [ 43181-78-8 ]
  • [ 63139-97-9 ]
  • 1-benzyl-N-((2-methylthiazol-5-yl)methyl)-1H-benzo[d]imidazol-2-amine [ No CAS ]
  • 66
  • [ 131052-58-9 ]
  • [ 43181-78-8 ]
  • 1-benzyl-N-(isoxazol-3-ylmethyl)-1H-benzo[d]imidazol-2-amine [ No CAS ]
  • 67
  • [ 43181-78-8 ]
  • 5-(1-benzyl-1H-benzimidazole-2-oxy)benzo[c][1,2]oxaborolan-1(3H)-alcohol [ No CAS ]
  • 68
  • [ 43181-78-8 ]
  • 2-bromo-5-(1-benzyl-1H-benzimidazole-2-oxy)-benzylalcohol [ No CAS ]
  • 69
  • [ 43181-78-8 ]
  • 5-(1-Benzyl-1H-benzimidazole-2-oxy)-2-bromobenzyl acetate [ No CAS ]
  • 70
  • [ 43181-78-8 ]
  • 5-(1-benzyl-1H-benzimidazole-2-oxy)-2-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolane -2-yl)benzyl acetate [ No CAS ]
  • 71
  • [ 2973-80-0 ]
  • [ 43181-78-8 ]
  • 5-(1-benzyl-1H-benzimidazole-2-oxy)-2-bromobenzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% With sodium hydride; In N,N-dimethyl-formamide; at 120℃;Inert atmosphere; Step 2: Under a nitrogen atmosphere, 1.56 mg, 7.76 mmol of 2-bromo-5-hydroxybenzaldehyde and 1.88 g of 7.75 mmol of <strong>[43181-78-8]1-benzyl-2-chlorobenzimidazole</strong> were dissolved in NN-dimethylformamide. In 10 mL, then add 60%, 341 mg, 8.53 mmol of sodium hydride, and the mixture was stirred at 120 C overnight, then cooled, filtered, and the filtrate was added with water and ethyl acetate.The organic phase is concentrated, and the residue is purified by column chromatography to give 5-((1-benzyl-1H-benzimidazole-2)-oxy)-2-bromobenzaldehyde.The white solid was 0.95 g and the yield was 30%.
  • 72
  • [ 43181-78-8 ]
  • C22H18N2O2S [ No CAS ]
  • 73
  • [ 43181-78-8 ]
  • 1-benzyl-2-(2,3-dimethylbut-3-en-2-yl)-1H-benzo[d]imidazole [ No CAS ]
  • 74
  • [ 43181-78-8 ]
  • 1-benzyl-2-(((1S,4R)-2,2,3,3-tetramethyl-4-phenylcyclobutyl)sulfonyl)-1H-benzo[d]imidazole [ No CAS ]
  • 1-benzyl-2-((2,2,3,3-tetramethyl-4-phenylcyclobutyl)sulfonyl)-1H-benzo[d]imidazole [ No CAS ]
  • 75
  • [ 43181-78-8 ]
  • (E)-1-benzyl-2-(styrylthio)-1H-benzo[d]imidazole [ No CAS ]
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