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[ CAS No. 16635-95-3 ]

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Chemical Structure| 16635-95-3
Chemical Structure| 16635-95-3
Structure of 16635-95-3 * Storage: {[proInfo.prStorage]}

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Product Details of [ 16635-95-3 ]

CAS No. :16635-95-3 MDL No. :MFCD00082751
Formula : C14H16N2 Boiling Point : 353.9°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :212.29 g/mol Pubchem ID :110695
Synonyms :

Safety of [ 16635-95-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 16635-95-3 ]

  • Downstream synthetic route of [ 16635-95-3 ]

[ 16635-95-3 ] Synthesis Path-Downstream   1~5

  • 2
  • [ 29841-69-8 ]
  • [ 79-04-9 ]
  • [ 138051-07-7 ]
YieldReaction ConditionsOperation in experiment
89% With dmap; triethylamine In dichloromethane at 5 - 20℃; for 3h;
70% With potassium carbonate In chloroform at 20℃; for 3.5h; Cooling with ice; Synthesis of S-2 (1S, 2S)-1, 2-diphenylethane-1, 2-diamine (1.0 g, 4.7 mmol) wasdissolved in 30 mL of dried chloroform and cooled in the ice bath. 1.4 g (10 mmol) anhydrous K2CO3 was placed in the solution as th ebase. 2-Chloroacetyl chloride (1.6 g, 14.1 mmol) was dropwisely added to the mixture within 30 min. The mixture was then stirred at room temperature for 3 h. After filtration, the filtrate was collected and washed with 20 mL 10% HCl, saturated NaHCO3 and water respectively. The organic layer was dried over anhydrous Na2SO4 and the solvent was evaporated under reduced pressure.The residue was then purified by column chromatography on silicagel using CHCl3/MeOH (50:1) as eluent to obtain pure products a as a solid (1.20 g, 70%).
843 mg With dmap; triethylamine In dichloromethane for 3h; Ambient temperature;
  • 3
  • [ 29841-69-8 ]
  • [ 98-59-9 ]
  • [ 167316-27-0 ]
YieldReaction ConditionsOperation in experiment
88% With sodium hydroxide; In dichloromethane; at 0 - 5℃; for 3h;Inert atmosphere; Synthesis of Compound 2009: To a 2-L, three-neck, round-bottom flask equipped with a temperature probe, magnetic stir bar, nitrogen inlet, and addition funnel were added (lS,2S)-(-)-l,2-diphenylethylenediamine (20 g, 0.094 mol) and dichloromethane (160 mL). The mixture was cooled to 0-3 0C and a 1 M solution of sodium hydroxide (160 mL) was added dropwise while maintaining the temperature below 5 0C. To this mixture was added a solution of toluenesulfonyl chloride (17.9 g, 0.094 mol) in dichloromethane (320 mL) dropwise over a 2-h period. The biphasic mixture was stirred at 0-5 0C for an additional 1 h and the reaction was deemed complete by TLC (50% EtO Ac/heptane, UV). Phases were separated and the organic phase was washed with water (2 x 320 mL) and brine (320 mL), dried over sodium sulfate and concentrated to a crude solid. The solid was dissolved in toluene (200 mL) at 70-80 0C and heptane (300 mL) was added portionwise while maintaining this temperature. The resulting slurry was cooled and stirred at 20-25 0C for 1 h and then cooled and stirred at 0-5 0C for 10 min. The solids were filtered and washed with a 50% solution of toluene in heptane (3 x 1 bed volume) to give compound 2009 (30.24 g, 88%) as a white powder.
82.3% With sodium hydroxide; In dichloromethane; water; at 0 - 20℃; for 3h; The procedure is the same as in Example 1,Except that (1S, 2S) -1,2-diphenylethylenediamine (3.0 g, 14.1 mmol)Added to 50mLDCM,After stirring and dissolving,A 15 mL aqueous solution of 2N NaOH was added,Cooling to 0 ,A solution of p-toluenesulfonyl chloride (2.65 g, 14.1 mmol)In dichloromethane (30 mL)After maintaining the reaction at 0 C for 1 hour,The temperature was raised to room temperature for 2 hours,HPLC detection reaction ended.The reaction solution was poured into saturated sodium chloride solution (30 mL)Stir for 10 minutes,After stratification,The aqueous phase was extracted once with DCM (30 mL)Combine organic phase,dry,The dichloromethane was removed by distillation under reduced pressure,Get crude.Recrystallization from petroleum ether / ethyl acetate system gave yellow solid Compound I (4.48 g, 82.3%)
  • 4
  • [ 37942-07-7 ]
  • [ 16635-95-3 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
96% In ethanol at 20℃; for 24h; 2.2.1. Synthesis of S,S-DS and R,R-DS (1S,2S)-(-) -1,2-Diphenylethylenediamine (0.2124 g, 1 mmol) was dissolved in 10 mL of absolute ethanol and 2.0 equivalents of 3,5-Bis(tertbutyl)- salicylaldehyde (0.4882 g, 2 mmol) were then added. The color of the reaction mixture turned instantly yellow. After 24 h reaction at room temperature, the powder was filtered and washed by ethanol, and then vacuum dried to obtain pale yellow powders (620 mg, 96%) ( Scheme 1 ). 1 H NMR (400 MHz, CDCl 3 ) 13.58 (s, 1H), 8.39 (s, 1H), 7.31 (d, J = 2.4 Hz, 1H), 6.98 (d, J = 2.4 Hz, 1H), 1.42 (s, 10H), 1.22 (s, 10H) (Fig. S1a) and 13 C NMR (101 MHz, CDCl 3 ) 167.28, 158.00, 140.05, 139.85, 136.43, 128.30, 128.07, 127.43, 127.17, 126.36, 117.91, 80.17, 35.02, 34.06, 31.44, 29.48 (Fig. S1b) can be seen in electronic supplementary in- formation (ESI).
88% In methanol; dichloromethane at 25 - 30℃;
70% In ethanol for 3h; Heating;
In tetrahydrofuran; methanol for 4h; Reflux;
In tetrahydrofuran; ethanol for 4h; Reflux;
In ethanol Reflux;

  • 5
  • [ 29841-69-8 ]
  • [ 18506-04-2 ]
  • [ 858370-95-3 ]
YieldReaction ConditionsOperation in experiment
97% With triethylamine In dichloromethane for 0.166667h; Heating;
97% Stage #1: (S,S)-1,2-diphenyl-1,2-diaminoethane; 5-chloro-5H-dibenzo[a,d]cycloheptene In dichloromethane at 20℃; for 2.16667h; Stage #2: With potassium carbonate In dichloromethane; water
97% In dichloromethane at 20℃; for 2.16667h; 1 Synthesis of (S,S)-1,2-bis(5H-dibenzo[a,d]cyclohepten-5-yl)-1,2-diphenylethanediamine (S,S-DPENtrop2) 667 mg of 5H-dibenzo[a,d]cyclohepten-5-yl chloride (2.95 mmol, 2 eq.) were added at room temperature to 313 mg of (S,S)-diphenylethanediamine (1.47 mmol) in 20 ml of CH2Cl2. After 10 min, a white precipitate formed. The suspension was stirred for a further 2 h and concentrated, and the residue was extracted with 10% by weight aqueous potassium carbonate solution and CH2Cl2. The organic phase was removed and the aqueous phase was extracted twice more with CH2Cl2. The collected organic phases were dried over sodium sulfate and concentrated. Chromatography on silica gel with hexane/diethyl ether (3:2 by volume) and subsequently diethyl ether as eluents gave rise to 846 mg of DPENtrop2 (1.43 mmol, 97%) as a colourless foam. In CDCl3, the compound is present in a symmetrical (approx. 68%) and an asymmetrical (approx. 32%) conformation. Symmetrical form:1H NMR (300 MHz, CDCl3): δ=2.48 (d, J=7.8 Hz, 2H, NH), 3.09 (s, 2H, CHNTrop), 4.49 (d, J=7.8 Hz, 2H, CH(Ph)(NHTrop)), 6.36 (d, J=11.8 Hz, 2H, CHolefin), 6.72 (d, J=11.8 Hz, 2H, CHolefin), 6.83-7.47 (m, 26H, CHaryl). 13C NMR (75 MHz, CDCl3):δ=65.4 (2C, CHNTrop), 66.4 (2C, CH(Ph)(NHTrop)), 126.7 (2C, CHaryl), 126.8 (2C, CHaryl), 126.9 (2C, CHaryl), 127.6 (2C, CHaryl), 128.0 (4C, CHaryl), 128.2 (4C, CHaryl), 128.6 (2C, CHaryl), 129.3 (2C, CHaryl), 129.8 (2C, CHaryl), 129.9 (2C, CHaryl), 130.0 (2C, CHaryl), 130.2 (2C, CHolefin), 130.3 (2C, CHolefin), 133.6 (2C, Cquart), 133.8 (2C, Cquart), 139.3 (2C, Cquart), 140.1 (2C, Cquart), 141.0 (2C, Cquart). IR: v=3317 m, (NH), 3020 m, 1599 w, 1489 m, 1451 s, 1436 s, 1071 m, 797 s, 760 s, 697 s. MS (70 eV, m/z, %): 538 (44), 476 (50), 296 (27), 207 (18), 191 (100). Selected data of asymmetrical form:1H NMR (300 MHz, CDCl3): δ=2.78 (br, 1H, NH), 3.13 (br, 1H, NH), 3.37 (d, J=7.0 Hz, 1H, CH(Ph)(NHTrop)), 3.74 (s, 1H, CHNTrop), 3.74 (d, J=7.0 Hz, 1H, CH(Ph)(NHTrop)), 4.74 (d, J=5.1 Hz, 1H, CHNTrop), 6.82-7.38 (m, 25H, CHaryl ) 7.7 (d, J=7.8 Hz, 1H, CHaryl).
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