| 99% |
With triethylamine;boron trifluoride diethyl etherate; In chloroform; at 75℃; for 4.0h;Reflux; |
Dissolve 10 g (88.4 mmol) compound 2-thioethylamine hydrochloride (C15), 22 g (85 mmol) <strong>[76-84-6]triphenylmethanol</strong> (C2) and 14 mL (99.7 mmol) triethylamine in 100 mL chloroform. Then heat under reflux at 75 degrees Celsius and a catalyst 30 mL (239 mmol) borontrifluoride ethyl ether complex (C3) is slowly dropped into the mixture. Then continue heating under reflux for 4 hours. The solution is decompressed and condensed. Add methanol to dissolve and then the solution is condensed again. Next add sodium bicarbonate solution and stir the solution until a white precipitate forms. Then vacuum filter to obtain the precipitate (solid). After washing with water and drying, a solid product-compound C16 (27.9 g, 99%) is obtained.Analysis of the synthesis product: IR (neat) nu 3381 (NH2) cm-1. 1H NMR (CDCl3) delta 7.42 (m, 3 H, Ph), 7.30 (m, 12 H, Ph), 2.58 (t, J=6.6 Hz, 2 H, CH2N), 2.32 (t, J=6.6 Hz, 2 H, CH2S), 1.45 (br, 2 H, NH2). 13C NMR (CDCl3) delta 144.80, 192.52, 127.81 and 126.60 (Ph), 66.51 (CPh), 40.94 (CH2N), 36.09 (CH2S). MS m/z 319 (M+), 243 (M+-C6H5+1). |
| 99% |
With boron trifluoride diethyl etherate; triethylamine; In chloroform; for 4.0h;Reflux; |
In the step S10, for synthesis of 2-[(Triphenylmethyl)thio]ethylamine (compound C6), take 5 g (44.0 mmol) 2-thioethylamine hydrochloride (compound C1), 11.5 g (44.0 mmol) <strong>[76-84-6]triphenylmethanol</strong> (compound C2) and 7.4 mL (52.8 mmol) triethylamine (compound C3), all dissolve in 80 mL chloroform (compound C4). After being heated and refluxed, slowly drop catalyst -14.9 mL (118.8 mmol) borontrifluoride ethyl ether complex (compound C5) into solution and continue heating under reflux for 4 hours. After cooling down, wash with water solution of sodium bicarbonate (2×100 mL). The organic phase is dehydrated by Na2SO4 and then is concentrated under reduced pressure so as to obtain the product-compound C8 (14g, 99%).Analysis of the synthesis product-compound C6: IR (neat) nu 3381 (NH2) cm-1. 1H NMR (CDCl3) delta 7.42 (m, 3H, Ph), 7.30 (m, 12H, Ph), 2.58 (t, J=6.6 Hz, 2H, CH2N), 2.32 (t, J=6.6 Hz, 2H, CH2S), 1.45 (br, 2H, NH2). 13C NMR (CDCl3) delta 144.80, 192.52, 127.81 and 126.60 (Ph), 66.51 (CPh), 40.94 (CH2N), 36.09 (CH2S). MS m/z 319 (M+), 243 (M+-C6H5+1). |
| 99% |
With triethylamine;boron trifluoride diethyl etherate; In chloroform; at 75℃; for 4.0h; |
I. Synthesis of Compound 1 (2-[(Triphenylmethyl)thio]ethylamine)2-thioethylamine hydrochloride (10 g, 88.4 mmol), <strong>[76-84-6]triphenylmethanol</strong> (22 g, 85 mmol), and triethylamine (14 mL, 99.7 mmol) were dissolved in trichloromethane (100 mL). The solution was heated to reflux (75 C.), and then a catalyst borontrifluoride ethyl ether complex (30 mL, 239 mmol) was slowly added dropwise, and then heated to reflux for another 4 h. The solution was concentrated under vacuum, taken up in methanol, and then concentrated again. An aqueous sodium bicarbonate solution was added with stirring, and a white solid was precipitated immediately. The solution was filtered with suction, to obtain the solid, which was then washed with water and dried, to obtain Compound 1 (27.9 g, 99%).Analysis data of Compound 1 is as shown in FIG. 1A and FIG. 1B.IR (neat) v 3381 (NH2) cm-1. 1H NMR (CDCl3) delta 7.42 (m, 3H, Ph), 7.30 (m, 12H, Ph), 2.58 (t, J=6.6 Hz, 2H, CH2N), 2.32 (t, J=6.6 Hz, 2H, CH2S), 1.45 (br, 2H, NH2). 13C NMR (CDCl3) delta 144.80, 192.52, 127.81 and 126.60 (Ph), 66.51 (CPh), 40.94 (CH2N), 36.09 (CH2S). MS m/z 319 (M+), 243 (M+-C6H5+1). |
| 99% |
|
Synthesis of 2-[(Triphenylmethyl)thio]ethylamine Dissolve 2-thioethylamine hydrochloride (5 g, 44.2 mmol), <strong>[76-84-6]triphenylmethanol</strong> (11 g, 42.5 mmol) and triethylamine (7 mL, 49.9 mmol) in 100 mL chloroform. Heat and reflux until the solution temperature reaches a certain temperature, slowly drop a catalyst borontrifluoride ethyl ether complex (15 mL, 119.5 mmol) into the solution and continue heating and reflux for 4 hours. Then cool down, add sodium bicarbonate aqueous solution into the solution and stir the mixture. White solid product is precipitated out immediately. Get the solid by suction filtration, wash the solid with water, and dry the solid. Thus solid product 2-[(triphenylmethyl)thio]ethylamine (14.0 g, 99%) is obtained.Compound Data of the Product: [0050] IR (neat) v 3381 (NH2) cm-1. [0051] 1H NMR (CDCl3) delta 7.42 (m, 3H, Ph), 7.30 (m, 12H, Ph), 2.58 (t, J=6.6 Hz, 2H, CH2N), 2.32 (t, J=6.6 Hz, 2H, CH2S), 1.45 (br, 2H, NH2). [0052] 13C NMR (CDCl3) delta 144.80, 192.52, 127.81 and 126.60 (Ph), 66.51 (CPh), 40.94 (CH2N), 36.09 (CH2S). [0053] MS m/z 319 (M+), 243((CPh3)+). |
| 99% |
With boron trifluoride diethyl etherate; triethylamine; In chloroform; at 75℃; for 4.0h; |
taking 2-sulfur ethylamine hydrochloride (5 g, 44.2 mmol), triphenylcarbinol (11 g, 42.5 mmol) triethylamine (triethylamine) and (7 ml, 49.9 mmol), co-dissolved in chloroform (80 ml) in. Heating (75 C) catalyst drops slowly after the backflow of boron trifluoride/diethyl ether mixture (15 ml, 120 mmol), continue to heating reflux for 4 hours. Concentrated under reduced pressure, by adding methanol, then concentrated. Mixing an aqueous solution of sodium carbonate is added, a white solid precipitated immediately. Suction filtering to its solid, and then washing with water and drying the solid product obtained for the compound (1) (14g, 99%). |
| 99% |
With boron trifluoride diethyl etherate; triethylamine; In chloroform; for 4.0h;Reflux; |
Take and dissolve 5 g (44.2 mmol) 2-thioethylamine hydrochloride, 11 g (42.5 mmol) <strong>[76-84-6]triphenylmethanol</strong> and 7 mL (49.9 mmol) triethylamine in 80 mL trichloromethane (chloroform). After the solution being heated at 75 C. and refluxed, slowly drop 15 mL (120 mmol) boron trifluoride ethyl ether complex used as catalyst into the solution. The mixed solution is continuously heated to reflux for 4 hours. After vacuum evaporation, dissolve residue with methanol and concentrate the solution again. Add sodium bicarbonate aqueous solution and stir the mixture to get white solid precipitate. After vacuum filtration, take the solid. Wash the solid with water and then dry to get 14 g (99%) solid product (compound 1).Analysis of compound 1:IR (neat) 3381 (NH2) cm-1. 1H NMR (CDCl3) 7.42 (m, 3 H, Ph), 7.30 (m, 12 H, Ph), 2.58 (t, J=6.6 Hz, 2 H, CH2N), 2.32 (t, J=6.6 Hz, 2 H, CH2S), 1.45 (br, 2 H, NH). 13C NMR (CDCl3) 144.80, 192.52, 127.81 & 126.60 (Ph), 66.51 (CPh), 40.94 (CH2N), 36.09 (CH2S). MS m/z 319 (M+), 243 (M+-C6H5+1). |
| 84% |
In trifluoroacetic acid; at 20℃; for 0.666667h; |
<strong>[76-84-6]Triphenylmethanol</strong> (2.29 g, 8.8 mmol) was added to a solution of 2-aminoethanethiol hydrochloride 8 (1.0 g, 8.8 mmol) in 4 mL trifluroaceticacid (TFA). The resulted solution was stirred at room temperature for about 40 min. TFA was removed in vacuo. The residue was triturated with ethyl ether. The formed white precipitate was filtered, partitioned with aqueous NaOH (25 mL, 1 M) and extracted with ethyl acetate. The organic layers were dried over anhydrous Na2SO4. After evaporation, the compound 9 was obtained as white solid (2.35 g, 7.4 mmol, 84%). 1H NMR (400 MHz,CD3OD) d 7.46e7.41 (m, 6H, ArH), 7.34e7.27 (m, 6H, ArH), 7.26e7.21(m, 3H, ArH), 2.54e2.44 (m, 4H, -NCH2-, -SCH2-). |
| 84% |
With trifluoroacetic acid; at 20℃; for 0.666667h; |
In a one-neck flask, 4 ml of trifluoroacetic acid was added followed by the compound cysteamine hydrochlorideSalt N1 (1.0 g, 8.8 mmol) followed by trityl alcohol (2.29 g, 8.8 mmol) slowly and stirred at room temperature for 40 min. The reaction was quenched to remove trifluoroacetic acid, followed by addition of anhydrous ether. A white solid appeared and was filtered. The filter cake was washed with 25 mM NaOH (aq), extracted with ethyl acetate and dried to give 2.35 g of a white powdery solid , Yield 84%. |
| 81% |
|
Compound 17 was prepared by an adaption of the procedure reported by Maltese et al. [47]. A solution of trityl alcohol (1.95 g, 7.5 mmol) and cysteamine hydrochloride (0.937 g, 8.25 mmol) in trifluoroacetic acid (7.5 mL) was stirred for 3 h at room temperature. The volatiles were evaporated under reduced pressure, and the crude residue basified (circa. pH 10) with saturated aqueous Na2CO3 solution. The aqueous mixture was extracted with CH2Cl2 (3 × 10 mL), the organic layer was dried (MgSO4) and evaporated under reduced pressure. The residue was then purified by flash column chromatography [MeOH:CH2Cl2 (10:90)] to give compound 17 (1.94 g, 81%) as a white powder. Mpt: 87-90 C (lit. 90-93 C from petroleum ether) [48]. 1H NMR (500 MHz): delta (MeOD): 2.32-2.36 (m, 2H, CH2), 2.41-2.45 (m, 2H, CH2), 7.19-7.24 (m, 3H), 7.25-7.31 (m, 6H), 7.39-7.41 (m, 6H). 13C NMR (125 MHz): delta (MeOD): 6.11, 41.56, 67.77, 127.79, 128.89, 130.78, 146.34. HRMS-ESI (+ve): Calculated for C21H22NS (M + H)+: 320.1467, found 320.1466. Elemental analysis: Found: C, 78.96; H, 6.63; N, 4.20 (Required for C21H21NS: C, 78.95; H, 6.63; N, 4.38). |
| 62% |
In ethyl acetate; trifluoroacetic acid; |
Part A Preparation of S-Triphenylmethyl-2-aminoethanethiol A solution of cysteamine hydrochloride (79.5 g, 0.7 mol) in TFA (500 ml) was treated with <strong>[76-84-6]triphenylmethanol</strong> (182 g, 0.7 mol), and stirred at room temperature for one hour. TFA was removed under reduced pressure at a temperature of 45 C. and the resulting dark orange oil was dissolved in EtOAc (700 ml). The EtOAc solution was washed with cold 2N NaOH (3*350 ml), H2O (2*350 ml), saturated NaHCO3 (350 ml), and saturated NaCl (350 ml). The combined aqueous washings were back extracted with EtOAc (350 ml). The combined organic layers were dried (MgSO4) and concentrated to a yellow solid. Trituration with ether (500 ml) gave product (97.2 g, 43%) as a colorless solid, MP 90-92 C. Concentration of the ether triturant to a volume of 100 ml and cooling produced an additional 40.9 g of product, MP 89-91 C., for a combined yield of 62%. |
| 62% |
In ethyl acetate; trifluoroacetic acid; |
Part A S-Triphenylmethyl-2-aminoethanethiol A solution of cysteamine hydrochloride (79.5 g, 0.7 mol) in TFA (500 ml) was treated with <strong>[76-84-6]triphenylmethanol</strong> (182 g, 0.7 mol), and stirred at room temperature for one hour. TFA was removed under reduced pressure at a temperature of 45 C. and the resulting dark orange oil was dissolved in EtOAc (700 ml). The EtOAc solution was washed with cold 2N NaOH (3*350 ml), H2 O (2*350 ml), saturated NaHCO3 (350 ml), and saturated NaCl (350 ml). The combined aqueous washings were back extracted with EtOAc (350 ml). The combined organic layers were dried (MgSO4) and concentrated to a yellow solid. Trituration with ether (500 ml) gave product (97.2 g, 43%) as a colorless solid, MP 90-92 C. (D. Brenner et al., J. Inorg. Chem. 1984, 23, 3793-3797, MP 93-94 C.). Concentration of the ether triturant to a volume of 100 ml and cooling produced an additional 40.9 g of product, MP 89-91 C., for a combined yield of 62%. |
| 62% |
In ethyl acetate; trifluoroacetic acid; |
Part A Preparation of S-Triphenylmethyl-2-aminoethanethiol A solution of cysteamine hydrochloride (79.5 g, 0.7 mol) in TFA (500 ml) was treated with <strong>[76-84-6]triphenylmethanol</strong> (182 g, 0.7 mol), and stirred at room temperature for one hour. TFA was removed under reduced pressure at a temperature of 45C andthe resulting dark orange oil was dissolved in EtOAc (700 ml). The EtOAc solution was washed with cold 2N NaOH (3 X 350 ml), H2O (2 X 350 ml), saturated NaHCO3(350 ml), and saturated NaCl (350 ml). The combined aqueous washings were back extracted with EtOAc (350 ml). The combined organic layers were dried (MgSO4) and concentrated to a yellow solid. Trituration with ether (500 ml) gave product (97.2 g, 43%) as a colorless solid, MP 90-92C. Concentration of the ether triturant to a volume of 100 ml and cooling produced an additional 40.9 g of product, MP 89-91C, for a combined yield of 62%. |
| 57% |
With trifluoroacetic acid; at 20℃; for 2.0h; |
To a scintillation vial under ambient atmosphere was added cysteamine hydrochloride (C3) (363 mg, 3.20 mmol), a stir bar, and trifluoroacetic acid (2 mL). The mixture was stirred and <strong>[76-84-6]triphenylmethanol</strong> (814 mg, 3.13 mmol) was added in portions (addition resulted in a deep sanguine reddening of the reaction mixture). The reaction mixture was allowed to stir at room temperature for 2 h before most of the solvent was evaporated under a stream of nitrogen. The resulting thick, gummy liquid was added to water (30 mL) and solid K2C03 was added until the residual acid was neutralized (pH paper). The resulting solid/liquid mixture was extracted with CH2C12 (3 x 20 mL; addition of CH2C12 resulted in dissolution of all solids), dried over MgSC^, filtered, and evaporated under reduced pressure to give a pale yellow solid. The material was redissolved in CH2C12 {ca. 5 mL) and purified by MPLC (4 g silica cartridge; 0-10% MeOH in CH2C12). The fractions that were estimated to have the desired material were combined and evaporated overnight to yield the pure material as an off-white solid (571 mg, 57%). Spectral data were consistent with the literature |
|
With sodium hydroxide; acetic acid; In hydrogenchloride; dichloromethane; water; |
(iv) Compound 81 A solution of 2-aminoethanethiol.HCl 80 (11.4 g, 100 mmol), <strong>[76-84-6]triphenylmethanol</strong> (TrOH, 26.0 g, 100 mmol) in HCl (37%, 44.8 mL) and acetic acid (280 mL) was stirred for 5 h at 40 C. The reaction mixture was concentrated in vacuo and the resulting white solid was washed with ether and dissolved in H2 O/CH2 Cl2 (1:1). After adjusting the pH of the aqueous layer to ca. 14 with 1 N NaOH, the desired compound was removed by extraction. The combined organic layers were dried (K2 CO3), filtered, and concentrated in vacuo to provide a white solid, S-(triphenylmethyl) 2-aminoethanethiol (28.8 g, 90.0 mmol, 90% from 80). Rf =0.50 (1:9 MeOH/CH2 Cl2); 1 H NMR (DMSO-d6) delta7.35-7.20 (m, 15H), 2.43 (t, J=6.1, 2H), 2.15 (t, J=5.9, 2H). |
|
In trifluoroacetic acid; |
E. 2-(Triphenylmethylthio)ethylamine (IX) A mixture of 2-mercaptoethylamine hydrochloride (11.45 g, 0.10 mol) and <strong>[76-84-6]triphenylmethanol</strong> (26.23 g, 0.10 mol) in trifluoracetic acid (100 ml) was stirred at room temperature for 30 minutes, then evaporated to a brown oil. Trituration of the oil with ether (500 ml) (complete color discharge) gave the trifluoroacetate salt of compound (IX) as a white precipitate which was filtered off and washed with ether. |
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