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[ CAS No. 1135-12-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 1135-12-2
Chemical Structure| 1135-12-2
Chemical Structure| 1135-12-2
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Product Details of [ 1135-12-2 ]

CAS No. :1135-12-2 MDL No. :MFCD00047861
Formula : C13H13N Boiling Point : -
Linear Structure Formula :- InChI Key :WDTRNCFZFQIWLM-UHFFFAOYSA-N
M.W : 183.25 Pubchem ID :136914
Synonyms :

Calculated chemistry of [ 1135-12-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.08
Num. rotatable bonds : 2
Num. H-bond acceptors : 0.0
Num. H-bond donors : 1.0
Molar Refractivity : 60.3
TPSA : 26.02 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.19 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.11
Log Po/w (XLOGP3) : 3.14
Log Po/w (WLOGP) : 2.87
Log Po/w (MLOGP) : 3.34
Log Po/w (SILICOS-IT) : 3.18
Consensus Log Po/w : 2.93

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.46
Solubility : 0.064 mg/ml ; 0.000349 mol/l
Class : Soluble
Log S (Ali) : -3.36
Solubility : 0.0807 mg/ml ; 0.000441 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.96
Solubility : 0.00201 mg/ml ; 0.000011 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.17

Safety of [ 1135-12-2 ]

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

Application In Synthesis of [ 1135-12-2 ]

* 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 [ 1135-12-2 ]

[ 1135-12-2 ] Synthesis Path-Downstream   1~83

  • 2
  • [ 80936-82-9 ]
  • phenylmagnesium bromide [ No CAS ]
  • [ 1135-12-2 ]
  • 3
  • [ 1137-41-3 ]
  • [ 1135-12-2 ]
YieldReaction ConditionsOperation in experiment
68% With aluminum (III) chloride; lithium aluminium tetrahydride; In diethyl ether; at 0 - 20℃; for 3h; To a mixture of LiAlH4 (10.0 equiv) in Et2O (5ml/mmol) was added the solution of AlCl3 (10.0 equiv) in Et2O (10ml/mmol) slowly at 0C, and the reaction mixture was stirred for 5min. Then the solution of (4-aminophenyl)(phenyl)methanone (12h, 1.0 equiv) in Et2O (15ml/mmol) was added, and the mixture was stirred at room temperature for 3h. After completion (monitored by TLC), the mixture was diluted using 6M HCl and neutralized by saturated sodium bicarbonate solution. Next, the solution was partitioned between water and ethyl acetate (3×). The organic layer was dried over magnesium sulfate anhydrous, filtered and concentrated in vacuo. The solid was purified by column chromatography to give the key intermediate 12f in 68% yield (Scheme S1).
With aluminum (III) chloride; lithium aluminium tetrahydride; In diethyl ether; at 0 - 20℃; for 3h; After LiAlH4 (10mmol, 379.5mg) was added to the reaction flask, placed after about 15min at 0 C AlCl3 (10 mmol, 1333 mg) in ether (15 ml) was added dropwise to the reaction and the mixture was stirred at 0 C for 5 min. A solution of p-aminobenzophenone (5a, 1 mmol, 197.2 mg) in ether (15 ml) was added dropwise to the reaction and the reaction was allowed to proceed to room temperature for 3 h. After completion of the reaction by TLC, the reaction solution was washed with 6 M HCl After dilution, the residue was neutralized with saturated NaHCO3 and the aqueous layer was extracted with ethyl acetate (20 ml X). The combined organic layers were dried over anhydrous Na2SO4 and concentrated to give intermediate 5b.
  • 4
  • [ 33675-70-6 ]
  • [ 602-56-2 ]
  • [ 35452-03-0 ]
  • [ 1135-12-2 ]
  • [ 122-39-4 ]
  • 5
  • [ 129075-89-4 ]
  • [ 100-58-3 ]
  • [ 1135-12-2 ]
YieldReaction ConditionsOperation in experiment
48% In benzene for 48h; Heating;
  • 6
  • [ 141883-37-6 ]
  • [ 1135-12-2 ]
  • 7
  • [ 623-10-9 ]
  • [ 71-43-2 ]
  • [ 1135-12-2 ]
  • [ 42308-28-1 ]
  • [ 13480-37-0 ]
  • 8
  • [ 1135-12-2 ]
  • [ 87-13-8 ]
  • [ 24805-59-2 ]
YieldReaction ConditionsOperation in experiment
at 130℃; for 2h; Preparation of Intermediate 3b. <strong>[1135-12-2]4-benzylaniline</strong> (Aldrich, 5g, 0.0273moles, 1 eq) and diethyl ethoxymethylenemalonate (Aldrich 5.5ml, 0.0273moles, 1 eq) were mixed in a round bottom flask. The mixture was heated for about 3 hours at 12O0C before reaction went to completion. (TLC hexane/ethylacetate, 7:3). Ethanol formed in the reaction was removed in vacuo. The crude was characterised by 1H-NMR confirming the desired structure. The compound was used for the next step without purification.
  • 9
  • [ 1135-12-2 ]
  • [ 112888-43-4 ]
  • (4-(N-((3,4-dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl)amino)phenyl)phenylmethane [ No CAS ]
  • 10
  • 4'-aminobenzophenone hydrochloride [ No CAS ]
  • [ 1135-12-2 ]
  • 11
  • [ 1135-12-2 ]
  • [ 79-08-3 ]
  • N-[4-(phenylmethyl)phenyl]glycine [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% With triethylamine; In DMF (N,N-dimethyl-formamide); at 100℃; for 24h; Preparation XXXVI N-[4-(phenylmethyl)phenyl]glycine A solution of 18.3 g (0.1 mol) of <strong>[1135-12-2]4-benzylaniline</strong> in 150 ml of dimethylformamide is prepared and 20.5 g (0.12 mol) of bromoacetic acid are added, followed by 14 ml of triethylamine. The reaction mixture is stirred for 24 hours at 100 C. and then cooled and poured into 200 ml of iced water. The mixture is extracted with 2 times 200 ml of ethyl acetate and the combined organic phases are washed and then dried over sodium sulfate and concentrated under reduced pressure. The crude product is purified by chromatography on silica gel using a cyclohexane/ethyl acetate mixture (95/5; v/v) as the eluent to give the expected compound in the form of beige crystals (yield=43%). M.p.=148 C.
  • 12
  • [ 1135-12-2 ]
  • [ 7250-67-1 ]
  • (4-benzyl-phenyl)-(2-pyrrolidin-1-yl-ethyl)-amine [ No CAS ]
  • 13
  • [ 1135-12-2 ]
  • [ 21584-72-5 ]
  • [ 530-62-1 ]
  • 4-(6,7-dimethoxy-quinazolin-4-yl)-piperazine-1-carboxylic acid (4-benzyl-phenyl)-amide [ No CAS ]
  • 14
  • [ 85888-81-9 ]
  • [ 1135-12-2 ]
  • <i>N</i>-(4-benzyl-phenyl)-2-chloromethyl-benzamide [ No CAS ]
  • 15
  • [ 463-71-8 ]
  • [ 1135-12-2 ]
  • [ 26328-58-5 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate; In tetrahydrofuran; water; at 23℃; General procedure: A solution of the arylamine derivative in THF was added to saturated NaHCO3 aqueous solution. Then a solution of CSCl2 in THF was added dropwise and the resulting mixture was stirred at 23 C for 2 h, TLC showed that there was no starting material left. To the above solution, the amine derivative was added dropwise at 0-10 C. When TLC indicated that the reaction was complete, the solution was extracted with MTBE three times and the organic phase was dried over anhydrous Na2SO4, filtered and evaporated to dryness to produce a crude product. After re-crystallizationin MTBE, a pure product was obtained.
  • 17
  • [ 1135-12-2 ]
  • 4-benzylphenylaminomethylenebisphosphonic acid [ No CAS ]
  • 18
  • [ 1135-12-2 ]
  • [ 372-31-6 ]
  • [ 733812-32-3 ]
YieldReaction ConditionsOperation in experiment
56% A stirred solution of <strong>[1135-12-2]4-benzylaniline</strong> (4.03 g, 22.0 mmol) in PhMe (100 ML) was treated with a PhMe (20 mL) solution of CF3COCH2CO2ET (4.15 g, 22.5 mmol). The reaction mixture was heated under reflux for 30 min, then more CF3COCH2CO2ET (1.25 g, 6.8 mmol) was added. The solution was heated under reflux for a further 2 h & the solvent removed under reduced pressure. The residual brown oil was dissolved in cold H2S04 (30 ML), then the mixture was heated at 90 C for 1 h. On cooling, the reaction mixture was poured onto crushed ice (100 g). The solid produced was collected & dried to give 4- (2-OXO-4-TRIFLUOROMETHYL-1, 2- DIHYDROQUINOLIN-6-YLMETHYL) -BENZENESULFONIC ACID (4.70 G, 56%): ON ( (CD3) 2SO) = 6.95 (S, 1H), 7.20 (d, 2H), 7.40 (d, 1H), 7.45-7. 60 (m, 4H). A vigourously stirred solution of this compound (1.92 g, 5.0 mmol) in anhydrous CH2C12-DMF (2: 1,60 mL) was treated dropwise with a solution of (COC1) 2 (3.17 g, 25.0 mmol) in anhydrous CH2C12 (47 ML). When LCMS indicated the reaction was complete, the solution was concentrated & the residue dissolved in Et2O (250 ML). The ET20 solution was washed with H20 (80 ML), back-extracting with more Et2O (80 ML). The combined organic extracts were dried (MGS04), filtered, & concentrated. The residue was treated with PE & the title compound (1.41 g, 70%) collected: M/Z (ES+) = 402.1 [M + H] +
56% A stirred solution of <strong>[1135-12-2]4-benzylaniline</strong> (4.03 g, 22.0 mmol) in PhMe (100 mL) was treated with a PhMe (20 mL) solution of CF3COCH2CO2Et (4.15 g, 22.5 mmol). The reaction mixture was heated under reflux for 30 minutes, then more CF3COCH2CO2Et (1.25 g, 6.8 mmol) was added. The solution was heated under reflux for a further 2 h and the solvent removed under reduced pressure. The residual brown oil was dissolved in cold H2SO4 (30 mL), then the mixture was heated at 90 C. for 1 h. On cooling, the reaction mixture was poured onto crushed ice (100 g). The solid produced was collected and dried to give 4-(2-oxo-4-trifluoromethyl-1,2-dihydroquinolin-6-ylmethyl)-benzenesulfonic acid (4.70 g, 56%): deltaH ((CD3)2SO)=6.95 (s, 1H), 7.20 (d, 2H), 7.40 (d, 1H), 7.45-7.60 (m, 4H). A vigourously stirred solution of this compound (1.92 g, 5.0 mmol) in anhydrous CH2Cl2-DMF (2:1, 60 mL) was treated dropwise with a solution of (COCl)2 (3.17 g, 25.0 mmol) in anhydrous CH2Cl2 (47 mL). When LCMS indicated the reaction was complete, the solution was concentrated & the residue dissolved in Et2O (250 mL). The Et2O solution was washed with H2O (80 mL), back-extracting with more Et2O (80 mL). The combined organic extracts were dried (MgSO4), filtered, and concentrated. The residue was treated with PE and the title compound (1.41 g, 70%) collected: mlz (ES+)=402.1 [M+H]+.
  • 19
  • [ 1135-12-2 ]
  • [ 50675-57-5 ]
  • [ 422322-12-1 ]
YieldReaction ConditionsOperation in experiment
71% With triethylamine; In dichloromethane; at 20℃; To a dichloromethane solution of 4-aminodiphenyl-methane (183 mg, 1 mmol), there were in order added triethylamine (about 3 equivalents) and dimethyl-cyclopropanecarboxylic acid chloride (about 2.2 equivalents) and the resulting mixture was stirred at room temperature overnight. Water was added to the mixture, the resulting mixture was extracted with ethyl acetate, the resulting extract was washed with a hydrochloric acid solution, water and a saturated aqueous sodium chloride solution, followed by drying the extract over anhydrous sodium sulfate and concentration thereof under reduced pressure. The resulting oily substance was purified by silica gel column chromatography to thus obtain a compound of Example 1 as crystals (197 mg, yield: 71%). [0093] 1H-NMR (300 MHz, CDCl3) delta=0.79-0.82 (1H, m), 1.18-1.22 (7H, m), 1.38-1.42 (1H, m), 4.76 (2H, s), 7.10-7.20 (4H, m), 7.23-7.25 (2H, m), 7.42-7.44 (3H, m). [0094] MS (ESI) m/z: 280 (M+H)+.
  • 20
  • [ 1135-12-2 ]
  • [ 6160-65-2 ]
  • [ 26328-58-5 ]
YieldReaction ConditionsOperation in experiment
88% In DMF (N,N-dimethyl-formamide); at 0 - 5℃; for 5h; Preparation XXXIII 1-Isothiocyanato-4-(phenylmethyl)benzene A solution of 5 g (27 mmol) of 4-(phenylmethyl)aniline in 20 ml of dimethylformamide is prepared and a solution of 5.77 g (29 mmol) of 1,1'-thiocarbonyldiimidazole in 20 ml of dimethylformamide is added at 0 C., with stirring. The reaction medium is stirred for 5 h at 5 C. and then poured into iced water. The mixture obtained is extracted twice with 100 ml of dichloromethane and the combined organic phases are washed with water and then dried over sodium sulfate and concentrated under reduced pressure. The residue is purified by chromatography using cyclohexane as the eluent to give the expected product in the form of an oil, which crystallizes in the refrigerator (yield=88%). M.p.<50 C.
  • 21
  • [ 1135-12-2 ]
  • [ 535-11-5 ]
  • [ 677778-51-7 ]
YieldReaction ConditionsOperation in experiment
97% With sodium hydrogencarbonate; at 140℃; for 5h;Neat (no solvent); Preparation XXXIV N-[4-(phenylmethyl)phenyl]alanine ethyl ester 3 g (16.4 mmol) of 4-(phenylmethyl)aniline and 4.3 ml (32.7 mmol) of ethyl 2-bromopropionate are mixed and 2.06 g (24.6 mmol) of sodium bicarbonate are added. The mixture is stirred for 5 h at 140 C. and then cooled and taken up with 50 ml of water and 100 ml of ethyl ether. After decantation, the aqueous phase is re-extracted with 50 ml of ethyl ether. The combined organic phases are washed with water and then dried over sodium sulfate and concentrated under reduced pressure. The residue is purified by chromatography on silica gel using a methylcyclohexane/ethyl acetate mixture (8/2; v/v) as the eluent to give 4.5 g of the expected product in the form of an orange-yellow oil (yield=97%). 1H NMR (300 MHz, DMSO): 7.17 (m, 5H); 6.91 (d, 2H); 6.45 (d, 2H); 5.80 (d, 1H); 4.07 (q, 2H); 3.96 (q, 1H); 3.75 (s, 2H); 1.34 (d, 3H); 1.14 (t, 3H).
  • 22
  • [ 2052-01-9 ]
  • [ 1135-12-2 ]
  • 2-methyl-N-[4-(phenylmethyl)phenyl]alanine [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% Preparation XXXVII 2-Methyl-N-[4-(phenylmethyl)phenyl]alanine 183 g (1 mol) of <strong>[1135-12-2]4-benzylaniline</strong> and 294 g (3.5 mol) of sodium bicarbonate are intimately mixed in a mortar. The mixture is placed in a reactor equipped with a robust stirrer, and 600 g (3 mol) of 2-bromo-2-methylpropionic acid are added. The mixture is stirred for one hour at 90 C. and then cooled and poured into 2 l of cold water. The hydrolysis medium is acidified slowly to pH 4 with concentrated hydrochloric acid. The precipitate formed is filtered off, washed with water and dried in a vacuum oven to give the expected compound in the form of pale pink crystals (yield=83%). M.p.=130 C.
  • 23
  • [ 1135-12-2 ]
  • [ 129121-46-6 ]
YieldReaction ConditionsOperation in experiment
1.06 g (88%) With bromine; potassium thioacyanate; In acetic acid; EXAMPLE 206 2-Amino-6-benzyl-benzothiazole A solution of <strong>[1135-12-2]4-benzylaniline</strong> (0.916 g, 5.00 mmol) and KSCN (0.97 g, 10.0 mmol, 2.0 eq) in 10 mL acetic acid was cooled at about 5 C., and was treated dropwise with a solution of bromine (0.258 mL, 5.00 mmol, 1.0 eq) in 2 mL acetic acid. The mixture was stirred at room temperature for about 1 hour. The precipitate was filtered off and washed with Et2O. The obtained solid was neutralized with saturated sodium carbonate solution, and a new precipitate was formed. It was filtered off, washed with water and MeOH, and dried under vacuum to give the desired compound 1.06 g (88%). LC/MS 241.2 (M+1); LC retention time 2.46 min.
  • 24
  • [ 1135-12-2 ]
  • [ 12775-96-1 ]
  • [ 497-19-8 ]
  • [ 75092-30-7 ]
  • [ 499791-95-6 ]
YieldReaction ConditionsOperation in experiment
4.86 g (50%) In dimethyl sulfoxide; Step 1. 4-[(4-Benzylphenyl)amino]-1-methyl-1H-pyrazole-5-carboxylic acid A mixture of <strong>[75092-30-7]4-iodo-1-methyl-1H-pyrazole-5-carboxylic acid</strong> ((Manaev, Yu. A. et al., J. Gen. Chem. USSR (Engl. Transl.), 1982, 52 (11), 2291), 8.0 g, 31.74 mmol), 4-benzylaniline (21.03 g, 114.76 mmol) and copper powder (3.2 g) in a mixture of 5% aqueous sodium carbonate (160 ml) and dimethylsulfoxide (80 ml) was stirred for 17 h at 100 C. After cooling to room temperature, the mixture was filtered through a pad of Celite, which was washed with water, 2N aqueous sodium hydroxide and diethyl ether. The separated water layer was washed with diethyl ether (100 ml*2). The water layer was acidified with concentrated hydrochloric acid and the formed solid was collected by filtration, dried, to give 4.86 g (50%) of the pure title compound as a pale brown solid. Rf value: 0.50 (methanol/dichloromethane/acetic acid=1/10/2 drops). 1H-NMR (DMSO-d6) delta: 7.63 (1 H, s), 7.50 (1 H, br s), 7.31-6.96 (9 H, m), 4.00 (3 H, s), 3.85 (2 H, s). One signal was not observed.
  • 25
  • [ 1135-12-2 ]
  • [ 503183-01-5 ]
YieldReaction ConditionsOperation in experiment
82.8% 17. 242 mg of 4-[(4-benzylphenyl)hydrazono]-4H-pyrazole-3,5-diamine was prepared in two steps starting with 183 mg (1.0 mmol) of 4-benzylphenylamine. Yield 82.8%. MS (m/z, ES+): 293 (M+1).
  • 26
  • [ 1135-12-2 ]
  • [ 364793-57-7 ]
  • 4-(4-benzylanilino)-7-bromo-3-quinolinecarbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With pyridine hydrochloride; In 1-ethoxyethanol; REFERENCE EXAMPLE 9 4-(4-Benzylanilino)-7-bromo-3-quinolinecarbonitrile A mixture of 4-aminodiphenylmethane (604 mg, 3.3 mmol), <strong>[364793-57-7]7-bromo-4-chloro-3-quinolinecarbonitrile</strong> (800 mg, 3.0 mmol) and pyridine hydrochloride (30 mg) in 15 nL of ethoxyethanol was heated at reflux for I hour. The mixture was cooled, poured into 5% sodium carbonate solution, and stirred. The product was filtered, washed with water, and dried to provide 1.20 g (96% yield) of 4-(4-benzylanilino)-7-bromo-3-quinolinecarbonitrile as a tan solid, mp 195-197 C; 1H NMR (DMSO-d6) delta 3.99 (s, 2H), 7.26 (mn, 9H), 7.81 (dd, J=9, 2 Hz, 1H), 8.12 (d, J=2 Hz, 1H), 8.41 (d, J=9 Hz, 1H), 8.57 (s, 1H), 9.91 (s, 1H); MS (ES) m/z 416.1 (M+1). Analysis for C23Hl6 BrN3: Calcd: C, 66.68;H, 3.89; N, 10.14. Found: C, 66.67;H, 3.96; N, 9.81.
  • 27
  • [ 1135-12-2 ]
  • [ 237385-69-2 ]
YieldReaction ConditionsOperation in experiment
62% a) Amino[4-benzylphenyl]amino}methane-1-thione <strong>[1135-12-2]4-Benzylphenylamine</strong> (500 mg, 2.73 mmol) was treated as described in Example 177, step (a) to give 410 mg (62% yield) of amino[4-benzylphenyl]amino}methane-1-thione. 1H NMR (DMSO-d6, 300 MHz) delta3.89 (s, 2 H), 7.14-7.28 (m, 9 H), 9.59 (s, 1 H); Mass Spectrum (ESI) m/z calcd. for C14H14N2S3, 242.1 (M+H), found 243.2.
62% a) Amino[4-benzylphenyl]amino}methane-1-thione <strong>[1135-12-2]4-Benzylphenylamine</strong> (500 mg, 2.73 mmol) was treated as described in Example 177, step (a) to give 410 mg (62% yield) of amino [4-benzylphenyl]amino}methane-1-thione. 1H NMR (DMSO-d6, 300 MHz) delta 3.89 (s, 2H), 7.14-7.28 (m, 9H), 9.59 (s, 1H); Mass Spectrum (ESI) m/z calcd. for C14H14N2S3, 242.1 (M+H), found 243.2.
  • 28
  • [ 4530-20-5 ]
  • [ 1135-12-2 ]
  • [ 68641-49-6 ]
  • [ 7087-68-5 ]
  • [ 254882-75-2 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; (A) N-tert-Butoxycarbonylglycine 4-Benzylphenylamide <strong>[68641-49-6]Bis(2-oxo-3-oxazolidinyl)phosphinic chloride</strong> (1.90 g) and N,N-diisopropylethyl-amine (1.5 mL) were added to a solution of 4-aminodiphenylmethane (0.52 g) and N-tert-butoxycarbonylglycine (0.50 g) in dichloromethane (30 mL) at 0 C. After stiriing at 0 C. for 10 min and at room temperature for 17.5 hr, the solvent was removed in vacuo. The residue was diluted with 1 N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, saturated sodium hydrogen carbonate, and brine, dried over anhydrous sodium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1, v/v) to afford the title compound (0.81 g) as a colorless powder: 1H NMR (400 MHz, CDCl3) delta 1.47 (s, 9H), 3.90 (d, 2H), 3.94 (s, 2H), 7.12-7.21 (m, 5H), 7.28 (d, 2H), 7.41 (d, 2H).
  • 29
  • ammonium thiocyanate [ No CAS ]
  • [ 1135-12-2 ]
  • [ 129121-46-6 ]
YieldReaction ConditionsOperation in experiment
With sodium chloride; bromine; In water; acetic acid; ethyl acetate; PREPARATION 17 2-Amino-6-benzylbenzothiazole 11.2 ml of bromine were added dropWise to a solution of 39.7 g of <strong>[1135-12-2]4-benzylaniline</strong> and 33 g of ammonium thiocyanate in 400 ml of acetic acid at a temperature of from 12 to 18 C. After completion of the addition, the mixture was stirred at room temperature for 2 hours and then the solvent was distilled off. The residue was mixed with 600 ml of ethyl acetate and 300 ml of water and the mixture was neutralized by the addition of potassium carbonate powder The ethyl acetate layer was separated, washed with an aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The residual solid was recrystallized from ethyl acetate to give 37.6 g of the title compound melting at 173-175 C.
  • 30
  • [ 106-98-9 ]
  • [ 1135-12-2 ]
  • [ 7784-21-6 ]
  • 2,6-di-sec-butyl-4-benzylaniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
aluminium chloride; In hexane; ethyl acetate; 1.1.1.2. 2,6-di-sec-butyl-<strong>[1135-12-2]4-benzylaniline</strong> 81 g of <strong>[1135-12-2]4-benzylaniline</strong>, 1.2 g of aluminium powder, 3.6 g of anhydrous aluminium chloride and 100 g of but-1-ene are heated for 24 hours at +260 C. in an autoclave. After cooling, the reaction mass is poured into ice-cold dilute sodium hydroxide solution and taken up in ether. The ether phase is separated off, dried over sodium sulfate and subjected to fractional distillation; b.p. 130-134 C./0.03 torr. Chromatographic purification on silica gel using hexane/ethyl acetate as eluant affords the title compound of formula STR12 in the form of a colourless oil; refractive index nD24: 1.5579.
  • 31
  • [ 1135-12-2 ]
  • [ 503832-30-2 ]
YieldReaction ConditionsOperation in experiment
41% In N-(6,7-dibutoxy-4-methyl-2-quinazolinyl)guanidine; EXAMPLE 48 N-(6-benzyl-4-methyl-2-quinazolinyl)guanidine was made in the same manner as N-(6,7-dibutoxy-4-methyl-2-quinazolinyl)guanidine (see Example 1) except that <strong>[1135-12-2]4-benzylaniline</strong> was used in place of 3,4-dibutoxyaniline. Name: 6-benzyl-2,2,4-trimethyl-1,2-dihydroquinoline. (synthesised using Method B (41% yield)). Data: ESMS 263 (MH+); 1H NMR (CDCl3) delta 7.14 (t, 2H, J=7.5 Hz), 7.35-7.33 (m, 3H), 7.07 (s, 1H), 6.95 (d, 1H, J=7.8 Hz), 6.51 (dd, 1H, J=8.1, 0.9 Hz), 5.45 (br s, 1H), 4.02 (s, 2H), 2.11 (s, 3H), 1.399 (s, 3H), 1.395 (s, 3H).
  • 32
  • [ 1135-12-2 ]
  • [ 16269-66-2 ]
  • 4-(4-benzylanilino)thieno[3,2-d]pyrimidine hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
In isopropyl alcohol; Example 28 4-(4-Benzylanilino)thieno[3,2-d]pyrimidine hydrochloride 4-Chlorothieno[3,2-d]pyrimidine (0.060 g, 0.35 mmol) and <strong>[1135-12-2]4-aminodiphenylmethane</strong> (commercially available from K & K) (0.080 g, 0.44 mmol) were reacted in 2-propanol (5 ml) for 30 minutes according to Procedure A. The white solid obtained was 4-(4-benzylanilino)thieno[3,2-d]pyrimidine hydrochloride (0.070 g, 56%), m.p. 251-255 C.; (Found: C, 64.00; H, 4.45, N, 11.72. C19H15N3S.HCl.0.1H2O requires: C, 64.16; H, 4.59; N, 11.81%); deltaH [2H6]-DMSO 11.05 (1H, br s, NH), 8.81 (1H, s, 2-H), 8.43 (1H, d, J 8, 6-H or 7-H), 7.60-7.52 (3H, m, (6-H or 7-H), 2'-H, 6'-H), 7.35-7.20 (6H, m, 3'-H, 5'-H, 2"-H, 3"-H, 5"-H, 6"-H), 7.19 (1H, t, J 6, 4"-H), 3.95, (2H, s, CH2); m/z (%) 318 (100, M+1+); nmax (KBr disc)/cm-1 2570, 1630, 1595, 1485, 1475, 1365.
  • 33
  • [ 1135-12-2 ]
  • [ 73365-02-3 ]
  • [ 929917-58-8 ]
YieldReaction ConditionsOperation in experiment
85% EXAMPLE 41; Step 1; (R)-2-[(4-Benzyl-phenylamino)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester; To a solution of 4-benzyl aniline (200 mg, 1.1 mmol) in dichloroethane (1.5 mL) was added a solution of N-(t-butoxycarbonyl)-D-prolinal (239 mg, 1.2 mmol) in dichloroethane (1.5 mL) at 0-5 C. Sodium triacetoxyborohydride (393 mg, 1.85 mmol) was added to the above solution. Acetic acid (65 mg, 1.1 mmol) in dichloroethane (1 mL) was added dropwise, over a period of 5 min at 0-5 C. The reaction mixture was stirred at 0-10 C. for 3 h. The mixture was diluted with saturated aq NaHCO3 and extracted with dichloromethane. Organic layer was dried over anhy. MgSO4 and the solvent was removed in vacuo to obtain the crude mixture, which was purified by silica gel flash chromatography to obtain the title product (340 mg, 85%).
  • 34
  • [ 1144-74-7 ]
  • [ 1135-12-2 ]
  • 35
  • [ 1135-12-2 ]
  • [ 118129-60-5 ]
  • [ 1029434-06-7 ]
YieldReaction ConditionsOperation in experiment
With propionic acid; for 12h;Heating / reflux; Part A: Preparation of N,N'-bis(4-benzylphenylVl,7-dibromoperylene-3,4:9,10- bis(dicarboxiamide) (PDIPhIPh-BM[0179] 4-Benzylaniline (3.60 g, 19.62 mmol) was added in three portions to a suspension of l,7-dibromoperylene-3,4:9,10-dianhydride (3.00 g, 5.45 mmol) in propionic acid (56 mL). The reaction mixture was heated under reflux for 12 hours. After cooling to room temperature, the resulting solid was collected by filtration, washed with propionic acid and several times with MeOH, and dried overnight. The crude product (3.29 g) was used in the next step without further purification.[0180] M.p. > 300C (DMF); 1H NMR (CHCl3, 300 MHz): delta 9.56 (d, 2H, J = 8.1 Hz), 9.01 (s, 2H), 8.81 (d, 2H, J = 8.1 Hz), 7.54-7.30 (m, 18H), 4.24 (s, 4H); HRMS (calculated for: C50H28Br2N2O6 878.0416): 878.0408.
  • 36
  • [ 1135-12-2 ]
  • [ 38186-88-8 ]
  • [ 1038827-26-7 ]
YieldReaction ConditionsOperation in experiment
82% Step (a) 2-[(4-benzylphenyl)amino]-5-fluoronicotinic acid4-aminodiphenylmetliane (0.835 g, 4.56 mmoles), potassium carbonate (0.378 g, 2.74 mmoles), copper (0.015 g, 0.23 mmoles) and copper(I) bromide (0.033 g, 0.23 mmoles) were added to a stirred solution of <strong>[38186-88-8]2-chloro-5-fluoronicotinic acid</strong> (0.4 g, 2.28 mmoles) in N,N-dimethylformamide (5 mL). The solution was heated to 120 0C for a period of 2 h then the DMF was evaporated prior to aqueous workup. The resultant solid plug was dissolved in IM HCl (50 mL) and extracted three times into ethyl acetate (50 mL) which was then combined and dried with anhydrous sodium sulphate, filtered and concentrated in vacuo to give the crude product as a brown solid. The crude was redissolved in ethyl acetate (50 mL), washed three times with IM HCl (50 mL) then once with saturated aqueous sodium hydrogencarbonate solution (50 mL). The organic layer was again dried and concentrated to give the sub-title compound as a brown solid (603 mg, 82percent). APCI (Multimode) m/z: 323 [M+H]
  • 37
  • [ 1135-12-2 ]
  • [ 145013-05-4 ]
  • [ 1029802-05-8 ]
YieldReaction ConditionsOperation in experiment
81% With triethylamine; mercury dichloride; In dichloromethane; at 0 - 20℃; for 20h; 896 mg (3.3 mmol) of HgCl2 were added over a solution of 550 mg (3.0 mmol) of 4-benzyl-aniline, 830 mg (3.0 mmol) of N,N'-di(tert-butoxycarbonyl)thiourea and 1.3 mL (9.3 mmol) of TEA in DCM (5 mL) at 0oC The resulting mixture was stirred at 0oC for 1 h and 19 h more at room temperature. Usual work up followed by silica gel column chromatography, eluting with hexane:EtOAc (5:2) gave 11a as a white solid (1.035 mg, 81% yield); mp 116-118oC.
  • 39
  • benzylzinc chloride-lithium chloride complex [ No CAS ]
  • [ 106-40-1 ]
  • [ 1135-12-2 ]
  • 40
  • [ 604000-97-7 ]
  • [ 1135-12-2 ]
  • [ 1133948-23-8 ]
YieldReaction ConditionsOperation in experiment
With N,N-diethyl-N-isopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; for 1h; N-(4-benzylphenyl)-2-fluoro-4-formylbenzamide To a solution of 4-benzylbenzenamine (0.100 g, 0.55 mmol), 2-fluoro-4-formylbenzoic acid (0.092 g, 0.55 mmol), N,N-diethylpropan-2-amine (0.10 ml, 0.65 mmol) in DMF (2.00ml) was added HBTU. The reaction mixture was stirred at room temperature for 1 h. The mixture was diluted with EtOAc, washed with water and dried over MgSO4. The solvent was evaporated and the residue was purified by flash chromatography in a EtOAc/Hexene system to give the title compound. MS (ESI) m/z: Calculated; 333.3: Observed; 332.1. 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 10.05-10.10(1 H, m), 8.31-8.44(2 H, m), 7.80-7.85 (1 H, m), 7.67-7.73 (1 H, m), 7.56-7.62 (2 H, m), 7.15-7.40 (6 H, m), 3.99 (2 H, s)
  • 41
  • [ 24415-66-5 ]
  • [ 1135-12-2 ]
  • [ 1141892-49-0 ]
  • 43
  • [ 116-81-4 ]
  • [ 1135-12-2 ]
  • [ 1052089-06-1 ]
  • 44
  • [ 1135-12-2 ]
  • [ 21168-41-2 ]
  • [ 1223002-96-7 ]
YieldReaction ConditionsOperation in experiment
65% In 1,4-dioxane; at 20 - 85℃; To a solution of Ethyl-4,6-dichloroquinoline-3-carboxylate (1.0 g, 3.7 mmol) in 1,4-dioxane (10 mL) was added a solution of 4-benzylbenzenamine (733 mg, 4.0 mmol) in 1,4-dioxane (10 mL) at room temperature. After stirred at 85 C 1 hour, the reaction mixture was then cooled down to room temperature and then treated with 20 mL of water. The resulting suspension treated with 10 NNaOH solutions to reach the pH about 9. It was partitioned between ethyl acetate and water. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. The crude product was purified by flash column chromatography using a 9:1 v/v hexane: ethyl acetate as solvent to afford title compound (1.1 g, 65 % yield) as a yellow solid.[00209] 1H NMR 600 MHz (DMSO-fc) delta 9.69 (s, 1H), 8.12 (d, J = 2.1 Hz, 1H), 7.91(d, J = 8.8 Hz, 1H), 7.74 (dd, J= 2.1, 6.7 Hz, 1H), 7.46 (m, 1H), 7.24 (m, 3H), 7.16 (m, 3H), 7.00 (d, J= 8.2 Hz, 2H), 3.90 (s, 2H), 3.86 (s, 1H), 3.84 (q, J= 7.0 Hz, 2H), 1.03 (/, J= 7.3 Hz, 3H), MS m/z 417.36 (M + 1).
  • 45
  • [ 24424-99-5 ]
  • [ 1135-12-2 ]
  • [ 1258545-02-6 ]
YieldReaction ConditionsOperation in experiment
77% With sodium carbonate; In dichloromethane; water; at 20℃; for 18h; Example 68; Synthesis of (3S)-3-amino-6-benzyl-1-hydroxy-3,4-dihydrocquinolin-2(1H)-one, trifluoroacetic acid salt (82); tert-Butyl (4-benzylphenyl)carbamate (73); To a solution of <strong>[1135-12-2]4-benzylaniline</strong> (12.5 g, 68.2 mmol) in a 1:1 solution of dichloromethane and saturated aqueous Na2CO3 was added (BOC)2O (16.5 g, 75 mmol). The reaction was allowed to stir at RT for 18 h. The reaction mixture was extracted with dichloromethane (3×200 mL), washed with water, dried over sodium sulfate, filtered and concentrated under reduced pressure to provide the product as a solid (14.8 g, 77%). 1H NMR (500 MHz, CDCl3) delta 1.51 (s, 9H), 3.93 (s, 2H), 6.41 (br s, 1H), 7.10-7.29 (m, 9H).
  • 46
  • N,N'-di(tert-butoxycarbonyl)imidazolidine-2-thione [ No CAS ]
  • [ 1135-12-2 ]
  • [ 1029801-98-6 ]
YieldReaction ConditionsOperation in experiment
78% With triethylamine; mercury dichloride; In dichloromethane; at 0 - 20℃; for 23h; 896 mg (3.3 mmol) of HgCl2 were added over a solution of 550 mg (3.0 mmol) of 4-benzyl-aniline, 907 mg (3.0 mmol) of N,N'-di(tert-butoxycarbonyl)imidazolidine-2-thione and 1.3 mL (9.3 mmol) of TEA in DCM (5 mL) at 0oC. The resulting mixture was stirred at 0oC. for 1 h and 22 h more at room temperature. Usual work up followed by neutral alumina column flash chromatography, eluting with hexane:EtOAc (2:1) gave a residue which was recrystallised from hexane to afford 4a as a white solid (1052 mg, 78% yield); mp 124-126oC.
  • 47
  • [ 1135-12-2 ]
  • [ 1393574-80-5 ]
  • [ 865-48-5 ]
  • [ 1414932-17-4 ]
  • 48
  • [ 1135-12-2 ]
  • [ 1145-59-1 ]
YieldReaction ConditionsOperation in experiment
Step C: Preparation of 4-(phenylmethyl)benzenesulfonyl chlorideTo 4-benzyianiline (2.0g, 10.9 mmol) in 20 mL of acetic acid and 20 mL of concentrated hydrochloric acid was added sodium nitrite (802 mg, 1 1 .6 mmol) in 5 mL of water dropwise while cooling in an ice bath. After stirring for 45 min this solution was added dropwise to a flask containing copper (1) chloride (0.4 g) and 20 mL acetic acid saturated with sulfur dioxide (3.0 mL). The reaction mixture was then allowed to stir at ambient temperature overnight. The reaction mixture was diluted with 200 mL of ethyl acetate and washed with saturated, aqueous sodium bicarbonate solution (3 x 50 mL). The ethyl acetate phase was separated and dried over magnesium sulfate and then concentrated under reduced pressure to obtain an oil. The crude product was chromatograped on silica gel using a gradient of hexane to hexane:ethyl acetate (95 :5) to provide 0.84 g of the title compound as an oilM l NMR (CDC33) 8 7.95 (d, '.:. . }. 7,41 (d, 2H), 7,33 (d, 2H), 7,28 (d, H i ) . 7, 18 (d, 21 . ) . 4,09 (s, 2H).
  • 49
  • [ 1135-12-2 ]
  • 4,7-dichloro-N-ethylquinolinium triflate [ No CAS ]
  • (E)-4-benzyl-N-(7-chloro-1-ethylquinolin-4(1H)-ylidene)aniline trifluoromethanesulfonate [ No CAS ]
  • 50
  • [ 1135-12-2 ]
  • [ 17823-69-7 ]
  • [ 1456732-73-2 ]
YieldReaction ConditionsOperation in experiment
Dissolved 0.500 g <strong>[17823-69-7]2-cyano-3,3-bis(methylthio)acrylamide</strong> in 15 mL EtOH and added 4-Aminodiphenylmethane (1.0 eq.) . Stirred reaction at 75 C until starting amide was absent by HPLC. Once complete (18 hrs), reaction was brought to room temperature and filtered to obtain a light yellow powder as product. Product was allowed to dry under vacuum for 1 hr. Product was then suspended in 10 mL EtOH and hydrazine hydrate (1 eq.) was added dropwise. Reaction was heated at 75 C until intermediate was absent (HPLC). Once intermediate was absent (18 hrs), reaction was brought to room temperature and filtered to obtain a yellow powder as product. Product was allowed to dry under vacuum for 1 hr. 5-amino-3-((4-benzylphenyl)amino)-lH-pyrazole-4-carboxamide
  • 51
  • [ 1135-12-2 ]
  • [ 65600-74-0 ]
  • [ 122-51-0 ]
  • diethyl N-4-benzylphenylaminomethylenebis(P-diethoxymethylphosphinate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% at 100 - 110℃; for 6h;Inert atmosphere; General procedure: Ethyl(diethoxymethyl)phosphinate (5.5g, 28 mmol), triethylorthoformate (2.33 ml, 14 mmol) and amine (14 mmol) were heated for 6h at 100-110C under nitrogenatmosphere. The mixture was evaporated and dissolved in chloroform. Then thecrude product was purified initially on silica gel column (chloroform/methanol)and then using flash chromatography (chloroform/methanol).
  • 52
  • [ 1135-12-2 ]
  • [ 74-88-4 ]
  • 4-benzyl-N,N,N-trimethylbenzenaminium iodide [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% With sodium carbonate; at 20℃; for 48h;Schlenk technique; Inert atmosphere; To a solution of sodium carbonate (0.4g, 3.77mmol) was added <strong>[1135-12-2]4-benzylaniline</strong> (0.732g, 4mmol) at room temperature followed by addition of CH3I (1.96g, 13.8mmol). The resulting mixture was refluxed for 48h to form a white precipitate, which was filtered, washed with ethanol, and dried in vacuo. Yield: 46%; mp: 198.5-199.2C; IR (KBr, disk): 3027, 3006, 2992, 2360, 2342, 1636, 1512, 1495, 1483, 1466, 1454, 1394, 1123, 1075, 1016, 950, 929, 859, 793, 744, 725, 702, 601, 547, 458cm-1; 1H NMR (400MHz, DMSO-d6): delta=7.89 (d, J=8.0Hz, 2H), 7.50 (d, J=8.0Hz, 2H), 7.31-7.20 (m, 5H), 4.03 (s, 2H), 3.59 (s, 9H); 13C NMR (100MHz, DMSO-d6): delta=139.8, 138.1, 135.0, 124.4, 123.2, 123.0, 120.7, 115.0, 50.8, 34.5.
  • 53
  • [ 1135-12-2 ]
  • [ 100-51-6 ]
  • [ 1616390-11-4 ]
YieldReaction ConditionsOperation in experiment
With Ti(NTf2)4; In toluene; at 160℃; for 1h;Microwave irradiation; Example 35 mol% of catalysts are blended with a solution comprising 1 molar equivalents of amine for 1 molar equivalent of alcohol and toluene as solvent (concentration of alcohol in solvent is 2 mol.L?) and 10 mol % ofligand. Reaction occurs under microwave irradiation at specified temperature and time.Results determined by ?H NMR analysis are mentioned in Table 3 N,4-dibenzylaniline: C20H19N / = 273.37 g/mol1H NMR (300 MHz, CDC13) 5 7.44-7.2 1 (m, 1OH), 7.08-7.05 (d, J 8.4 Hz,2H), 6.65-6.62 (d, 2H), 4.35 (s, 2H), 4.12 (br, 1H),.3.94 (s, 2H).13C NMR (75 MHz, CDC13) 5 146.6, 142.2, 139.7, 130.8, 129.9, 129.0,128.8, 128.6, 127.7, 127.4, 126.9, 113.2, 48.6, 41.3.
  • 54
  • [ 6728-26-3 ]
  • [ 1135-12-2 ]
  • [ 1370728-36-1 ]
  • [ 1629155-17-4 ]
  • 55
  • [ 1135-12-2 ]
  • [ 2365-48-2 ]
  • [ 530-62-1 ]
  • 3-(4-benzylphenyl)thiazolidine-2,4-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% In dichloromethane; at 20℃; for 72h; General procedure: The respective amine (1.1 equivalent) and methyl thioglycolate(1.0 equivalent) were added to an ice-cooled solution of 1,19-carbonyldiimidazole (1.1 equivalent) in 30 ml of absolute methylenechloride. The reaction mixture was stirred at room temperature for3 days and then washed three times with 3 M HCl. The solvent wasremoved, and the crude solid was purified by recrystallization fromtoluene or by flash column chromatography.
  • 56
  • [ 916482-29-6 ]
  • [ 1135-12-2 ]
  • ethyl 2-((4-((4-benzylphenyl)amino)-6-chloropyrimidin-2-yl)thio)octanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 60℃; for 24h; General procedure: The chlorinated ethyl [(pyrimidin-2-yl)sulfanyl] acetate derivatives (E1, 1 eq), the corresponding primary amine (E2, 1.2 eq) were dissolved in THF (7 ml) and N-ethyldiisopropylamine(3 eq) was added. The mixture was heated at 60C for 24h. The reaction mixture was cooled to room temperature and evaporated under reduced pressure to achieve the crude product. It was purified by column chromatography on silica gel (n-hexane- ethyl acetate) and finally recrystallized in EtOH.
87% With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 60℃; for 24h; General procedure: The chlorinated ethyl [(pyrimidin-2-yl)sulfanyl] acetate derivatives (E1, 1 eq), the corresponding primary amine (E2, 1.2 eq) were dissolved in THF (7 ml) and N-ethyldiisopropylamine (3 eq) was added. The mixture was heated at 60C for 24h. The reaction mixture was cooled to room temperature and evaporated under reduced pressure to achieve the crude product. It was purified by column chromatography on silica gel (n-hexane-ethyl acetate) and finally recrystallized in EtOH.
  • 57
  • [ 1135-12-2 ]
  • 2-((5-(4-(pyrrolidin-1-ylsulfonyl)phenyl)-1,3.4-oxadiazol-2-yl)thio)acetic acid [ No CAS ]
  • N-(4-benzylphenyl)-2-((5-(4-(pyrrolidin-1-ylsulfonyl)phenyl)-1,3,4-oxadiazol-2-yl)thio)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 18h; To a stirred solution of 2-((5-(4-(pyrrolidin-l-ylsulfonyl)phenyl)-l,3,4-oxadiazol-2- yl)thio)acetic acid (0.10 g, 0.30 mmol) in CH2CI2 (5 mL) was added l-[3- (dimethylamino)propyl]-3-ethyl carbodiimide hydrochloride (0.07 g, 0.40 mmol) and 4- benzylaniline (0.06 g, 0.30 mmol). Reaction was stirred at room temperature for 18 hours before being purified by flash silica chromatography to give N-(4-benzylphenyl)-2-((5-(4- (pyrrolidin-l-ylsulfonyl)phenyl)-l,3,4-oxadiazol-2-yl)thio)acetamide as a white solid (0.05 g, 30%). 1H NMR (600 MHz, DMSO) delta 10.41 (s, 1H), 8.20 - 8.16 (m, 2H), 8.00 - 7.95 (m, 2H), 7.49 (d, J = 8.5 Hz, 2H), 7.27 (t, J = 7.5 Hz, 2H), 7.19 (m, 5H), 4.35 (s, 2H), 3.89 (s, 2H), 3.18 (t, J = 6.7 Hz, 4H), 1.67 - 1.63 (m, 4H); 13C NMR (151 MHz, DMSO) delta 164.7, 164.5, 164.2, 141.4, 138.9, 136.7 (signals overlapping), 129.1, 128.6, 128.5, 128.3, 127.3, 126.7, 126.0, 119.4, 47.9, 40.5, 36.8, 24.8; [CI]+ calcd. for C27H27N4O4S2, 535.14737; found 535.1478.
  • 59
  • [ 1135-12-2 ]
  • [ 79-04-9 ]
  • N-(4-benzylphenyl)-2-chloroacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With triethylamine; In dichloromethane; at 20℃;Inert atmosphere; General procedure: In a dichloromethanesolution (2-3 mL) of chloroacetylchloride (1.1 eq), adichloromethane solution (8-10 mL) of the appropriate amine (1 eq) andtriethylamine (1.1 eq) was added dropwise and the reaction mixture was stirredovernight at room temperature under a nitrogen atmosphere. The reaction mixturewas evaporated and the residue was extracted with ethyl acetate-brine. Theorganic layer was dried over Na2SO4 and upon rotary evaporationgave the desired product, which was pure in most cases (by TLC). In certaincases, chromatography was applied for further purification
  • 60
  • [ 1135-12-2 ]
  • [ 79-04-9 ]
  • [ 19514-92-2 ]
YieldReaction ConditionsOperation in experiment
88% With potassium carbonate; In 1,2-dichloro-ethane; at 0℃; for 2h; General procedure: Chloroacetyl chloride (0.47 mL, 5.90 mmol) was addeddropwise to a stirred mixture of the appropriate aniline 5a-c(5.56 mmol) and K2CO3 (0.90 g, 6.51 mmol) in anhydrous DCE(20 mL) at 0 C. The reaction mixture was stirred for 2 h andallowed to warm to room temperature overnight. The inorganicmaterials were filtered through a pad of silica gel and washed withDCE (25 mL). The filtrate was evaporated under reduced pressureand the residue was purified by recrystallization from a mixtureof hexane/ethyl acetate (3:2).
  • 61
  • [ 1135-12-2 ]
  • [ 15486-96-1 ]
  • N-(4-benzylphenyl)-3-bromopropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With potassium carbonate; In dichloromethane; at 20℃; for 3h;Inert atmosphere; To a round-bottom flask under inert argon atmosphere was added 2-1 (3.65 g, 19.92 mmol, 1 equiv), followed by dichloromethane (200 mL), potassium carbonate (3.56 g, 25.78 mmol, 1.3 equiv), then 3-bromopropionyl chloride (3.59 g, 20.92 mmol, 1.05 equiv) while stirring at room temperature. After 90 minutes, the reaction was quenched with 2M NaOH (10 mL). Organic and aqueous phases were separated, then organic phase was washed with saturated aqueous sodium chloride (NaCl) solution. Organics were isolated, dried with magnesium sulfate and filtered through a coarse (40-60 micron) frit. Solvent was removed under reduced pressure to yield compound 2-2 (6.34 g, 19.92 mmol, 100% yield), and was used without further purification. Product was characterized by 1H NMR and 13C NMR on a Varian 500 MHz spectrometer in CDCl3
  • 62
  • [ 118-48-9 ]
  • [ 1135-12-2 ]
  • [ 78-39-7 ]
  • C22H18N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
In neat (no solvent); at 120℃; for 4h; General procedure: The equimolar mixture of isatoic anhydride 4 (0.41 g, 2.5 mmol), aniline 5 (0.23 g, 2.5mmol) and triethyl orthoacetate 6 (0.41 g, 2.5 mmol) was stirred magnetically at 120 C (oil bath temp) for 4 h followed by addition of benzaldehyde 7 (0.26 g, 2.5 mmol) and the stirring was continued for another 4 h (TLC). The crude reaction mixture was recrystallized from EtOH to obtain analytically pure 8a (0.21 g, 65%) as white solid; mp = 168-170 C.
  • 63
  • [ 1135-12-2 ]
  • 4-chloro-6-(2,2,2-trifluoroethyl)thieno[2,3-d]pyrimidine [ No CAS ]
  • N-(4-benzylphenyl)-6-(2,2,2-trifluoroethyl)thieno[2,3-d]pyrimidin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With N-ethyl-N,N-diisopropylamine; In isopropyl alcohol; at 100℃; for 4h; General procedure: To a solution of compound S9 (30 mg, 0.12 mmol, 1.0 equiv) in isopropanol (5 mL) was added compound S5 (1.1 equiv) and DIPEA (3 equiv). The mixture was stirred at 100 C for 4 h. The reaction mixture was cooled to RT and concentrated in vacuo. The residue was purified by flash chromatography (SiO2,DCM : MeOH = 20:1) to give the desired compound .
  • 64
  • [ 1135-12-2 ]
  • [ 2888-06-4 ]
  • N-(4-benzylphenyl)-3-chlorobenzenesulfonamide [ No CAS ]
  • 65
  • [ 1135-12-2 ]
  • [ 79-08-3 ]
  • C15H14BrNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: A mixture of 2-bromoacetic acid(1.0 equiv), 1-hydroxybenzotriazole (HOBT,1.0 equiv), 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride (EDCI, 1.0 equiv) and N,N-diisopropylethylamine (DIPEA, 1.5 equiv) in dichloromethane (DCM) was stirred at ambient temperature for 0.5h. To the solution of the mixture, different amines (1.0 equiv) were added, and the reaction mixture was continued to stir 10-12hat room temperature [32,33]. Upon completion of the reaction as determined by TLC, The mixture was concentrated and partitioned between water and ethyl acetate. The organic layer was dried over magnesium sulfate anhydrous, filtered and concentrated in vacuo. The products were purified bycolumn chromatography with appropriate eluents.
  • 66
  • [ 627-27-0 ]
  • [ 1135-12-2 ]
  • 4-((4-benzylphenyl)amino)butan-2-one [ No CAS ]
  • 67
  • [ 1135-12-2 ]
  • [ 3680-69-1 ]
  • N4-(4-benzylphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine [ No CAS ]
  • 69
  • [ 5281-18-5 ]
  • [ 540-37-4 ]
  • [ 1135-12-2 ]
  • 70
  • [ 5281-18-5 ]
  • [ 3899-93-2 ]
  • [ 1135-12-2 ]
  • 71
  • [ 924-44-7 ]
  • [ 1135-12-2 ]
  • C34H32N2O4 [ No CAS ]
  • 72
  • [ 1135-12-2 ]
  • [ 108-94-1 ]
  • N,N'-bis(4-benzylphenyl)-1,2-benzenediamine [ No CAS ]
  • 73
  • [ 6479-18-1 ]
  • [ 1135-12-2 ]
  • 3-(4-benzylphenyl)-1-methylquinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% General procedure: To a 25mL round bottle was added corresponding aryl aniline (4.0 equiv.) and 2.0 mL of anhydrous CH3CN, thentBuONO (6.0 equiv.) was added dropwise via syringe in an ice bath, followed by washing the syringe with CH3CN(0.5 mL x 2). After addition, the mixture was warmed and continued to stir at rt for 0.5 h (preparing in situArN2OBut). Then the ArN2OBut in CH3CN was transferred into an oven-dried Schlenk tube (25 mL) charged withcorresponding quinoxalin-2(1H)-one (1, 0.3 mmol, 1.0 equiv.), followed by washing the bottle with CH3CN (0.5mL x 2). The Schlenk tube was exchanged adequately by N2. Then, the mixture was stirred for 48 h at rt. The finialmixture was diluted by ethyl acetate and filtered through a pad of silica. The filtrate was concentrated underreduced pressure and the residue was purified by self-prepared silica plate (petroleum ether/ethyl acetate: 20/1 to10/1) to afford the desired product 3 as yellow or orange solid.
  • 74
  • [ 112-96-9 ]
  • [ 1135-12-2 ]
  • C32H50N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
13% In acetonitrile; at 90℃; for 120h;Inert atmosphere; In an argon atmosphere, <strong>[1135-12-2]4-aminodiphenylmethane</strong> (416mg, 2.27 mmol) was dissolved in acetonitrile (100 mE), octadecyl isocyanate (0.9 mE, 2.27 mmol) was added thereto, and the mixture was stirred at 90 C. for 5 days. After the completion of the reaction was confirmed by TEC, the solvent was concentrated, and the product precipitated as a solid was collected by filtration. The product was purified by a reprecipitation method with acetone-hexane to obtain a monourea compound of formula 10 as a white solid (amount: 171.5 mg, yield: 13%). 1H NMR (600 MHz, DMSO-d5) oe 0.85 (t, J6.9Hz, 3H), 1.23 (m, 30H), 1.39 (m, 2H), 3.03 (dt, J6.2, 6.5Hz, 2H), 3.38 (s, 2H), 6.07 (brs, 1H), 7.05 (d, J8.9 Hz, 2H),7.16-7.19 (m, 3H), 7.26 (d, J8.2 Hz, 2H), 7.27 (d, J8.3 Hz,2H), 8.31 (s, 1H).
  • 75
  • [ 101-53-1 ]
  • [ 1135-12-2 ]
  • 76
  • [ 1135-12-2 ]
  • [ 172646-45-6 ]
  • N-(4-benzylphenyl)-7-(diethylamino)-2-oxo-2H-chromene-3-carboxamide [ No CAS ]
  • 77
  • [ 1135-12-2 ]
  • [ 121-90-4 ]
  • C20H16N2O3 [ No CAS ]
  • 78
  • [ 1135-12-2 ]
  • trifluoromethyl 4-fluorobenzene-1-sulfonate [ No CAS ]
  • p-benzyl-α,α,α-trifluoromethoxybenzene [ No CAS ]
  • 79
  • [ 625-38-7 ]
  • [ 1135-12-2 ]
  • C21H19NO3 [ No CAS ]
  • C21H19NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tert.-butylhydroperoxide; 2.9-dimethyl-1,10-phenanthroline; palladium(II) trifluoroacetate; In acetonitrile; at 35℃; for 4h; 0.25 mmol of <strong>[1135-12-2]p-benzylaniline</strong> and 0.75 mmol of vinyl acetate were added to the reaction tube.10 mol% of Pd(TFA)2, 0.25 relative to the amount of <strong>[1135-12-2]p-benzylaniline</strong>Millol of tert-butyl peroxide, 15 mol% relative to the amount of <strong>[1135-12-2]p-benzylaniline</strong>2,9-Dimethyl-1,10-phenanthroline, 0.5 ml of acetonitrile, under air conditionsAfter stirring at 35 C for 4 hours, the heating and stirring were stopped, and the mixture was cooled to room temperature.The crude product is obtained by distillation under reduced pressure, and then purified by column chromatography to give the desired product.The column chromatography eluate used was n-hexane: ethyl acetate = 1:2 (volume ratio)The yield is 70%.The desired product obtained was two diastereomers, product 1 and product 2.
  • 80
  • [ 1622-32-8 ]
  • [ 1135-12-2 ]
  • N-(4-benzylphenyl)ethenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With triethylamine; In dichloromethane; at 0℃; for 2h; General procedure: 4-phenoxyphenol (186mg, 1mmol) was stirred with TEA (278muL, 2mmol) in Anhydrous DCM (10mL) at 0C, then 2-Chloroethanesulfonyl chloride (105muL, 1mmol) which was diluted with DCM (2mL) was slowly added into the mixture. The reaction mixture was stirred for 2h then evaporated. The residue was diluted and extracted with EtOAc then washed with water for 3 times. The organic layers were dried over Na2SO4 and evaporated. The residue was chromatographed (silicagel, Petroleum ether/EtOAc=3:1) to give 4-phenoxyphenyl ethenesulfonate (DC-TEADin03) (193mg, 70%) as a colorless oil.
  • 81
  • [ 1135-12-2 ]
  • C20H23NO2S [ No CAS ]
  • C32H32N2OS [ No CAS ]
  • 82
  • [ 50-00-0 ]
  • [ 1135-12-2 ]
  • [ 106-47-8 ]
  • [ 126-81-8 ]
  • [ 1122-91-4 ]
  • 1-(4-benzylphenyl)-2-(4-bromophenyl)-3-(4-chlorophenyl)-1,2,3,4,7,8-hexahydro-7,7-dimethylquinazolin-5(6H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% General procedure: The compounds were synthesized as following know steps: (a) dimedone 1 (5mmol, 700mg), primary amine 2 (5.5mmol), and AcOH (10mmol, 600muL) were added in a conical flask (125ml) with 20mL water and kept stirring for 2hat 70C; (b) amine 4 (15mmol), 38% formaldehyde 5 (7mmol, 560muL), and the mixture of aldehyde 3 (20mmol) and urea (1.5mmol, 90mg) (aldehyde 3 was dissolved using as little as possible of dichloromethane, then adding urea and shaking well) were successively added into the above mixture, and kept stirring at 70C for 12h; (c) After the reactions were completed, the product mixtures were extracted with dichloromethane three times. The organic phase was dried with anhydrous Na2SO4, filtered and evaporated under reduced pressure, then purified by preparative column chromatography with petroleum-ether-ethyl acetate (15:1?10:1?8:1?5:1?3:1?2:1) as eluent to afford the desired products OHQs in 51-90% yields.
  • 83
  • [ 1135-12-2 ]
  • [ 613-42-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 12.5 h / -78 - 20 °C / Schlenk technique; Inert atmosphere 2.1: tetrahydrofuran / 0.08 h / 20 °C / Schlenk technique; Inert atmosphere 2.2: 12.03 h / 70 °C / Schlenk technique; Inert atmosphere; Glovebox
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