Echemi Chemical 5-(4'-Methylbiphenyl-2-yl)-1-trityl-1H-tetrazole Description

1. CAS No:124750-53-4 Formula:C33H26N4 Synonyms:5-(4'-Methylbiphenyl-2-yl)-1-trityl-1H-tetrazole;5-[4'-METHYL (1,1'-BIPHENYL)-2-YL]-1-TRIPHENYLMETHYL-TETRAZOLE;n-(triphenylmethyl)-5-(4'-methylbiphenyl -2-yl-)terazole;N-(TRIPHENYLMETHYL)-5-(4'-METHYLBIPHENYL-2-YL)TETRAZOLE;5-(4'-Methyl-1,1'- biphenyl-2-yl)-1-triphenylmethyl-1H-tetrazole;5-[4''- Echemi Chemical 5-(4'-Methylbiphenyl-2-yl)-1-trityl-1H-tetrazole Description Off-white Solid Echemi Chemical 5-(4'-Methylbiphenyl-2-yl)-1-trityl-1H-tetrazole Basic Attributes CAS No：124750-53-4 Molecular Formula ：C33H26N4 Molecular Mass ：478.59 Exact Mass ：478.215759 PSA ：43.6 A^2 LogP ：8 InChIKeys ：ZSBYTGRKIKIRRJ-UHFFFAOYSA-N H-bond Acceptor ：3 H-bond Donor ：0 SP3 ：0.06 RBN ：6 Echemi Chemical 5-(4'-Methylbiphenyl-2-yl)-1-trityl-1H-tetrazole Characteristics Density ：1.13±0.1 g/cm3(Predicted) Melting Point ：166-169 °C(Solv: ethyl acetate (141-78-6); dichloromethane (75-09-2)) Bolling Point ：681.6±65.0 °C(Predicted) Flash Point ：366.0±34.3 °C Refractive Index ：1.645

2. Echemi Chemical 5-(4'-Methylbiphenyl-2-yl)-1-trityl-1H-tetrazole Product Usage An intermediate in the preparation of labelled Candesartan. Echemi Chemical 5-(4'-Methylbiphenyl-2-yl)-1-trityl-1H-tetrazole Production Methods Dissolve compound 2 (200 g) with stirring at 40°C700mL of acetone, Aqueous sodium hydroxide solution (40.67 g sodium hydroxide dissolved in 160 mL water) is added, Continue stirring for 1h, A solution of triphenylchloromethane in acetone (270.8 g of triphenylmethyl chloride dissolved in 800 mL of acetone) was initially added dropwise.The solid was added dropwise and gradually evolved into a white turbid liquid.The reaction was monitored by TLC until it was completely filtered off and washed with water to give a solid as intermediate 3.The solid was blow dried at 50°C to give white intermediate 3 (385 g), yield: 95.2percent, HPLC: 99.44percent.General procedure: A solution of the appropriate tetrazole 1 (10.0 mmol) in CH2Cl2 (5mL) was added to a solution of TrCl (3.1 g, 11.0 mmol), Et3N (2.5mL, 17.6 mmol), and DMAP (92 mg, 0.4 mmol) in CH2Cl2 (10 mL)at r.t., and the mixture was stirred overnight. The reaction was thenquenched with H2O (5 mL) and the mixture was extracted withEtOAc (3 × 15 mL). The organic phases were combined, washedwith brine (5 mL), dried (Na2SO4), and concentrated at 15 Torr. Theresidue was purified by column chromatography (deactivated silicagel, hexane–EtOAc) to give the expected tetrazoles 1a–f and 1i–l.For the preparation of the ditritylated compound 1g, the amounts ofthe reagents and solvents used were double those indicated above.General procedure: A solution of the corresponding tetrazole (10.0 mmol) in CH2Cl2 (5 mL) was added to a solution of trityl chloride (3.1 g, 11.0 mmol), 4-(dimethylamino)pyridine (92 mg, 0.4 mmol) in CH2Cl2 (10 mL) at room temperature and themixture was stirred overnight. The reaction was then quenched with water (5 mL) and extracted with ethyl acetate (3 15 mL) and thecombined organic phases were washed with brine (5 mL) and dried over sodium sulfate. After evaporation of the solvents (15 Torr), the resulting residue was purified by column chromatography (deactivated silica gel, hexane/ethyl acetate) affording the expectedtetrazoles 1a-1f and 1i-1l.For the preparation of the double tritylated compound 1g the amounts of the reagents and solvent used were double the ones triethylamine (2.5 mL, 17.6 mmol) and

3. indicatedabove. Compound 1g was separated by column chromatography [deactivated silica gel, hexane/ethyl acetate]. The correspondingphysical, spectroscopic and analytical data for the tritylated tetrazoles follow.General procedure: A solution of the corresponding tetrazole (10.0 mmol) in CHIn a 100 mL equipped with a magnetic stir, Reflux condenser was charged as shown in the formulaN- (triphenylmethyl)benzeneTetrazole, 1.94 g (5.0 mmol)Palladium / carbon (in terms of palladium), 0.106 g (1.0 mmol)(P-methylphenyl) iodotetrafluoroborate, 3.96 g (10.0 mmol)8.0 g (20.0 mmol) of sodium hydroxide was added, 40 ml of dichloroethane was added as a solvent, Heated to 80 ° C for 6 hours. After the reaction, The palladium / carbon was collected by filtration, The solvent was removed by distillation under reduced pressure, The residue was purified by column chromatography (silica gel: 200-300 mesh; mobile phase, petroleum ether: ethyl acetate = 10: 1, v / v) to afford the desired product as a white solid. obtain Of the product for2- (4-methylphenyl) -N- (triphenylmethyl) benzenetetrazole1.745g, The yield was 73percent