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Product Details of [ 1199-47-9 ]

CAS No. :1199-47-9 MDL No. :MFCD16996854
Formula : C10H15NO Boiling Point : -
Linear Structure Formula :- InChI Key :HFCOMOKKPQIADM-UHFFFAOYSA-N
M.W : 165.23 Pubchem ID :15294169
Synonyms :

Safety of [ 1199-47-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P270-P271-P272-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P333+P313-P337+P313-P363-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H302-H319-H335-H317 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1199-47-9 ]

* 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 [ 1199-47-9 ]

[ 1199-47-9 ] Synthesis Path-Downstream   1~40

  • 1
  • [ 1199-47-9 ]
  • [ 114791-07-0 ]
YieldReaction ConditionsOperation in experiment
With water; sodium acetate at 37℃; for 0.333333h;
  • 2
  • [ 1199-47-9 ]
  • [ 1034-39-5 ]
  • [ 76825-98-4 ]
YieldReaction ConditionsOperation in experiment
54%
  • 3
  • [ 1199-47-9 ]
  • [ 114791-07-0 ]
  • 4-Amino-1,7-di-tert-butyl-phenoxazin-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 35% 2: 48% With salcomine; oxygen In methanol at 25℃; for 1.5h;
YieldReaction ConditionsOperation in experiment
H-Brueckenbind. (Einfl. d. tert.-Butylgruppe);
YieldReaction ConditionsOperation in experiment
2-Nitro-5-tert.-butyl-phenol, H2 <Raney-Ni>;
(yield)94percent;
  • 6
  • [ 872595-54-5 ]
  • [ 1199-47-9 ]
  • 4-((4-tert-butyl-2-hydroxyphenylimino)methyl)-2H-benzofuro[3,2-g]chromen-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol for 2h; Heating;
  • 7
  • [ 5651-77-4 ]
  • 4-acetamido-3-acetoxy-1-tert.-butylbenzene [ No CAS ]
  • [ 1199-47-9 ]
YieldReaction ConditionsOperation in experiment
With acetic anhydride In pyridine; ethyl acetate 6 6-tert.-Butyl-4-[2-hydroxy-3-(2-propylamino)-propoxy]-2-benzimidazolinone By hydrogenation of 3-tert.-butyl-6-nitrophenol in aqueous ethanolic solution in the presence of palladiumcharcoal, there is obtained 6-amino-3-tert.-butylphenol (decomposition point 206°-208° C.) which, after acetylation with acetic anhydride in ethyl acetate/pyridine, gives 4-acetamido-3-acetoxy-1-tert.-butylbenzene (m.p. 109°-110° C.).
  • 8
  • [ 55-22-1 ]
  • [ 1199-47-9 ]
  • [ 1192020-96-4 ]
YieldReaction ConditionsOperation in experiment
With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 80℃; for 5h; 8 A mixture of 1.44 g of 2-amino-5-tert-butylphenol, 1.07 g of isonicotinic acid, 2.17 g of WSC and 15 ml of pyridine was stirred while heating at 80°C for five hours. The reaction mixture was cooled to room temperature, and then water was poured. Precipitated solid was filtered and washed with water and diethyl ether to give 1.22 g of N-(4-tert-butyl-2-hydroxyphenyl)isonicotinamide. [Show Image] 1H-NMR (CDCl3+DMSO-d6) δ: 9.32 (br s, 1H), 9.12 (br s, 1H), 8.81-8.77 (m, 2H), 7.85-7.78 (m, 3H), 7.03 (d, J=1.9, 1H), 6.93 (dd, J=8.5, 1.9 Hz, 1H), 1.3 (s, 9H)
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 80℃; for 5h; 8 Reference Production Example 8To a mixture of 5 g of 3-tert-butylphenol and 30 ml of acetic acid, a mixture of 3.0 g of 70% nitric acid and 10 ml of acetic acid was added dropwise with the temperature kept at 10-15° C. and stirred for two hours. The reaction mixture was poured into ice water and extracted with ethyl acetate twice. The combined organic layers were washed with water, a saturated aqueous solution of sodium hydrogencarbonate and a saturated sodium chloride solution, dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 1.82 g of 5-tert-butyl-2-nitrophenol.1H-NMR (CDCl3) δ: 10.60 (s, 1H), 8.01 (d, J=9.0 Hz, 1H), 7.13 (d, J=2.2, 1H), 7.01 (dd, J=9.0, 2.0 Hz, 1H), 1.33 (s, 9H)2-amino-5-tert-butylphenol was obtained according to the same manner as that of Reference Production Example 1, using 5-tert-butyl-2-nitrophenol instead of 4-propyl-2-nitrophenol.A mixture of 1.44 g of 2-amino-5-tert-butylphenol, 1.07 g of isonicotinic acid, 2.17 g of WSC and 15 ml of pyridine was stirred while heating at 80° C. for five hours. The reaction mixture was cooled to room temperature, and then water was poured. Precipitated solid was filtered and washed with water and diethyl ether to give 1.22 g of N-(4-tert-butyl-2-hydroxyphenyl)isonicotinamide.1H-NMR (CDCl3+DMSO-d6) δ: 9.32 (br s, 1H), 9.12 (br s, 1H), 8.81-8.77 (m, 2H), 7.85-7.78 (m, 3H), 7.03 (d, J=1.9, 1H), 6.93 (dd, J=8.5, 1.9 Hz, 1H), 1.31 (s, 9H)
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In pyridine at 80℃; for 5h; 8 A mixture of 1.44 g of 2-amino-5-tert-butylphenol, 1.07 g of isonicotinic acid,2.17 g of WSC and 15 ml of pyridine was stirred while heating at 80°C for five hours. The reaction mixture was cooled to room temperature, and then water was poured. Precipitated solid was filtered and washed with water and diethyl ether to give 1.22 g of N-(4-tert-butyl-2- hydroxyphenyl)isonicotinamide.-NMR (CDCl3+DMSO-d6) δ: 9.32 (br s, 1H), 9.12 (br s, 1H), 8.81-8.77 (m, 2H), 7.85-7.78 (m, 3H), 7.03 (d, J=1.9, 1H), 6.93 (dd, J=8.5, 1.9 Hz, 1H), 1.31 (s, 9H)
With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 80℃; for 5h; 8 A mixture of 1.44 g of 2-amino-5-tert-butylphenol, 1.07 g of isonicotinic acid, 2.17 g of WSC and 15 ml of pyridine was stirred while heating at 80°C for five hours. The reaction mixture was cooled to room temperature, and then water was poured. Precipitated solid was filtered and washed with water and diethyl ether to give 1.22 g of N-(4-tert-butyl-2- ;yphenyl)isonicotinamide.-NMR (CDCl3+DMSO-d6) δ: 9.32 (br s, 1H), 9.12 (br s, 1H), 8.81-8.77 (m, 2H), 7.85-7.78 (m, 3H), 7.03 (d, J=1.9, 1H), 6.93 (dd, J=8.5, 1.9 Hz, 1H), 1.31 (s, 9H)
With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 80℃; for 5h; 8 A mixture of 1.44 g of 2-amino-5-tert-butylphenol, 1.07 g of isonicotinic acid,2.17 g of WSC and 15 ml of pyridine was stirred while heating at 80°C for five hours. The reaction mixture was cooled to room temperature, and then water was poured. Precipitated solid was filtered and washed with water and diethyl ether to give 1.22 g of N-(4-tert-butyl-2- hydroxyphenyl)isonicotinamide.1 H-NMR (CDCl3+DMSO-d6) δ: 9.32 (br s, IH), 9.12 (br s, IH), 8.81-8.77 (m, 2H), 7.85-7.78 (m, 3H), 7.03 (d, J=1.9, IH), 6.93 (dd, J=8.5, 1.9 Hz, IH), 1.31 (s, 9H)
With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 80℃; for 5h; 8 A mixture of 1.44 g of 2-amino-5-tert-butylphenol, 1.07 g of isonicotinic acid,2.17 g of WSC and 15 ml of pyridine was stirred while heating at 80°C for five hours. The reaction mixture was cooled to room temperature, and then water was poured. Precipitated solid was filtered and washed with water and diethyl ether to give 1.22 g of N-(4-tert-butyl-2- hydroxyphenyl)isonicotinamide.1H-NMR (CDCl3+DMSO-d6) δ: 9.32 (br s, 1H), 9.12 (br s, 1H), 8.81-8.77 (m, 2H), 7.85-7.78 (m, 3H), 7.03 (d, J=1.9, 1H), 6.93 (dd, J=8.5, 1.9 Hz, 1H), 1.31 (s, 9H)
With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 80℃; for 5h; 8 A mixture of 1.44 g of 2-amino-5-tert-butylphenol, 1.07 g of isonicotinic acid,2.17 g of WSC and 15 ml of pyridine was stirred while heating at 80°C for five hours. The reaction mixture was cooled to room temperature, and then water was poured. Precipitated solid was filtered and washed with water and diethyl ether to give 1.22 g of N-(4-tert-butyl-2- hydroxyphenyl)isonicotinamide.1 H-NMR (CDCl3+DMSO-d6) δ: 9.32 (br s, IH), 9.12 (br s, IH), 8.81-8.77 (m, 2H), 7.85-7.78 (m, 3H), 7.03 (d, J=1.9, IH), 6.93 (dd, J=8.5, 1.9 Hz, IH), 1.31 (s, 9H)

  • 9
  • [ 55-22-1 ]
  • [ 1199-47-9 ]
  • [ 1192018-89-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 5 h / 80 °C 2: triethylamine; triphenylphosphine / tetrachloromethane / 3 h / Reflux
Multi-step reaction with 2 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / pyridine / 5 h / 80 °C 2: triethylamine; triphenylphosphine / tetrachloromethane / 3 h / Reflux
Multi-step reaction with 2 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 5 h / 80 °C 2: triethylamine; triphenylphosphine; tetrachloromethane / 3 h / Reflux
Multi-step reaction with 2 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 5 h / 80 °C 2: triethylamine; triphenylphosphine / tetrachloromethane / 3 h / Reflux

  • 10
  • [ 1199-47-9 ]
  • [ 532-27-4 ]
  • C18H19NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With iodine; potassium carbonate In tetrahydrofuran; water at 20℃; for 8h; Inert atmosphere; Green chemistry; General procedure for the synthesis of 1,4-benzoxazine 3: General procedure: A flame-dried round bottom flask was charged with o-aminophenol 1 (1 equiv), 2-chloro-1-phenylethanone 2 (1 equiv), and I2 (0.1 mmol) in 5 mL of THF/H2O (5:1)under positive pressure of nitrogen followed by addition of K2CO3 (3 equiv).The resulting solution was stirred for 7-8 h at room temperature (Table 2).After completion of the reaction (monitored by TLC), the reaction mixture wasquenched with satd aq Na2SO3 until the iodine color almost disappeared and was extracted with CHCl3. The organic layer was washed with satd aq NaHCO3and brine, and dried over Na2SO4. Then the combined organic layer was concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel using hexane/EtOAc (10:1) as eluent toafford analytically pure sample of 3. The structure of products was confirmed by comparison of their mp, TLC, IR, and 1H, 13C NMR data with authentic samples obtained commercially or prepared by the literature methods.6,12
  • 11
  • [ 1199-47-9 ]
  • [ 2196-99-8 ]
  • C19H21NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With iodine; potassium carbonate In tetrahydrofuran; water at 20℃; for 8h; Inert atmosphere; Green chemistry; General procedure for the synthesis of 1,4-benzoxazine 3: General procedure: A flame-dried round bottom flask was charged with o-aminophenol 1 (1 equiv), 2-chloro-1-phenylethanone 2 (1 equiv), and I2 (0.1 mmol) in 5 mL of THF/H2O (5:1)under positive pressure of nitrogen followed by addition of K2CO3 (3 equiv).The resulting solution was stirred for 7-8 h at room temperature (Table 2).After completion of the reaction (monitored by TLC), the reaction mixture wasquenched with satd aq Na2SO3 until the iodine color almost disappeared and was extracted with CHCl3. The organic layer was washed with satd aq NaHCO3and brine, and dried over Na2SO4. Then the combined organic layer was concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel using hexane/EtOAc (10:1) as eluent toafford analytically pure sample of 3. The structure of products was confirmed by comparison of their mp, TLC, IR, and 1H, 13C NMR data with authentic samples obtained commercially or prepared by the literature methods.6,12
  • 12
  • [ 19213-72-0 ]
  • [ 1199-47-9 ]
  • [ 31554-71-9 ]
  • 13
  • 4,4''-dihydroxy-5,5''-dimethoxy-[1,1':4',1''-terphenyl]-3,3''-dicarbaldehyde [ No CAS ]
  • [ 1199-47-9 ]
  • 3,3''-bis((E)-((4-(tert-butyl)-2-hydroxyphenyl)imino)methyl)-5,5''-dimethoxy-[1,1':4',1''-terphenyl]-4,4''-diol [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% In methanol Reflux;
  • 14
  • [ 893638-52-3 ]
  • [ 1199-47-9 ]
  • C25H19F6NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With oxygen; 4-methoxy-2,2,6,6-tetramethylpiperidin-1-oxyl radical In m-xylene at 120℃; for 8.5h; Schlenk technique; Inert atmosphere;
  • 15
  • [ 17754-90-4 ]
  • [ 1199-47-9 ]
  • C21H28N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% Reflux;
  • 16
  • [ 1199-47-9 ]
  • [ 589-15-1 ]
  • 2-((4-bromobenzyl)thio)-6-(t-butyl)benzo[d]oxazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% Stage #1: 2-amino-5-(tert-butyl)phenol With Thiram In water at 120℃; Green chemistry; Stage #2: 1-bromomethyl-4-bromobenzene With potassium carbonate In water at 80℃; for 1h; Green chemistry;
  • 17
  • C11H15NO4 [ No CAS ]
  • [ 1199-47-9 ]
  • [ 104-87-0 ]
  • dimethyl 1-(4-(tert-butyl)-2-hydroxyphenyl)-2-(p-tolyl)-1,2-dihydropyridine-3,5-dicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With trifluoroacetic acid In acetonitrile at 20℃;
  • 18
  • C11H15NO4 [ No CAS ]
  • [ 1199-47-9 ]
  • [ 1122-91-4 ]
  • dimethyl 2-(4-bromophenyl)-1-(4-(tert-butyl)-2-hydroxyphenyl)-1,2-dihydropyridine-3,5-dicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With trifluoroacetic acid In acetonitrile at 20℃;
  • 19
  • [ 1199-47-9 ]
  • C25H25BrNO5(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: trifluoroacetic acid / acetonitrile / 20 °C 2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.08 h / 20 °C
  • 20
  • [ 1199-47-9 ]
  • C26H28NO5(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: trifluoroacetic acid / acetonitrile / 20 °C 2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.08 h / 20 °C
  • 21
  • [ 1199-47-9 ]
  • methyl 5-(4-bromobenzoyl)-1-(4-(tert-butyl)-2-hydroxyphenyl)-6-oxo-1,6-dihydro-pyridine-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: trifluoroacetic acid / acetonitrile / 20 °C 2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.08 h / 20 °C 3: potassium carbonate; water / tetrahydrofuran / 48 h / 20 °C
  • 22
  • [ 1199-47-9 ]
  • methyl 1-(4-(tert-butyl)-2-hydroxyphenyl)-5-(4-methylbenzoyl)-6-oxo-1,6-dihydro-pyridine-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: trifluoroacetic acid / acetonitrile / 20 °C 2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.08 h / 20 °C 3: potassium carbonate; water / tetrahydrofuran / 48 h / 20 °C
  • 23
  • [ 1199-47-9 ]
  • (Z)-methyl 1-(4-(tert-butyl)-2-hydroxyphenyl)-5-(hydroxy(p-tolyl)-methylene)-6-oxo-1,2,5,6-tetrahydropyridine-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: trifluoroacetic acid / acetonitrile / 20 °C 2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.08 h / 20 °C 3: potassium carbonate; water / tetrahydrofuran / 48 h / 20 °C 4: sodium tetrahydroborate; methanol / 20 °C
  • 24
  • [ 1199-47-9 ]
  • C17H17Br3 [ No CAS ]
  • C27H30BrNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
With polyphosphoric acid at 180℃; 1 Add 0.015mol of reactant D-1, 0.015mol of intermediate C-1 and 120ml of polyphosphoric acid to a 250ml flask, and heat to reflux for 6-9 hours at 180°C. After the reaction is complete, cool to room temperature naturally, and add 50ml with a volume ratio of 5 : 3 water and n-hexane mixed solvent, stir, stand still, filter, dry the filter cake, recrystallize with water and petroleum ether in a volume ratio of 5:3 to obtain intermediate E-1.
  • 25
  • [ 1199-47-9 ]
  • C54H48BN3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: polyphosphoric acid / 180 °C 2.1: bromine; acetic acid / 5 h / 0 - 20 °C / Inert atmosphere 3.1: tetrahydrofuran / 0 - 20 °C / Inert atmosphere 4.1: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine / toluene / 110 - 120 °C / Inert atmosphere 5.1: tert.-butyl lithium / 2 h / 60 °C / Inert atmosphere 5.2: 1 h / 20 °C
  • 26
  • [ 1199-47-9 ]
  • C36H40N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: polyphosphoric acid / 180 °C 2: bromine; acetic acid / 5 h / 0 - 20 °C / Inert atmosphere 3: tetrahydrofuran / 0 - 20 °C / Inert atmosphere 4: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine / toluene / 110 - 120 °C / Inert atmosphere
  • 27
  • [ 1199-47-9 ]
  • C30H36N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: polyphosphoric acid / 180 °C 2: bromine; acetic acid / 5 h / 0 - 20 °C / Inert atmosphere 3: tetrahydrofuran / 0 - 20 °C / Inert atmosphere
  • 28
  • [ 1199-47-9 ]
  • C22H18Br2N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: polyphosphoric acid / 180 °C 2: bromine; acetic acid / 5 h / 0 - 20 °C / Inert atmosphere
  • 29
  • [ 1199-47-9 ]
  • C17H18Br2 [ No CAS ]
  • C27H31NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
With polyphosphoric acid at 180℃; 8 Add 0.015 mol of intermediate C-8, 0.015 mol of reactant D-8 and 120 ml of polyphosphoric acid to a 250 ml flask, heat to reflux at 180°C for 6-9 hours, the reaction is complete, cool to room temperature naturally, and add 50 ml of volume ratio 5 : 3 water and n-hexane mixed solvent, stirring, standing, filtering, drying the filter cake, recrystallizing with water and petroleum ether in a volume ratio of 5:3 to obtain intermediate E-8.
  • 30
  • [ 1199-47-9 ]
  • C12H7Br2N [ No CAS ]
  • C22H20N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With polyphosphoric acid at 180℃; 14 Add 0.015mol of reactant A-14, 0.015mol of reactant B-14 and 120ml of polyphosphoric acid to a 250ml flask, heat to reflux at 180°C for 6-9 hours, the reaction is complete, naturally cool to room temperature, add 50ml with a volume ratio of 5 :3 water and n-hexane mixed solvent, stir, stand still, filter, dry the filter cake, recrystallize with water and petroleum ether in a volume ratio of 5:3 to obtain intermediate C-14
  • 31
  • [ 1199-47-9 ]
  • N-(6-(tert-butyl)benzo[d]oxazol-2-yl)-4-methyl-1,2,3-thiadiazole-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: methanol 2.1: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0 °C 2.2: 20 °C
  • 32
  • [ 506-68-3 ]
  • [ 1199-47-9 ]
  • 6-(tert-butyl)benzo[d]oxazol-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% In methanol 5.2.3 General procedure for the synthesis of benzoxazol-2-amino compounds (1b-12b, 25b, 27b-29b) General procedure: BrCN (2.03g, 17.6mmol, 1.1eq) was slowly added to a solution of 2-aminophenol (16.0mmol, 1.0 eq) in 30mL MeOH. The reaction mixture was stirred overnight at room temperature. Excess BrCN was quenched with saturated Na2CO3 in a fume hood, until the pH value reached ∼7. Then, MeOH was evaporated and EtOAc (30mL) was added. The organic phase was washed with water (20mL×2) and brine (20mL), and then it was dried over anhydrous Na2SO4, filtered, and evaporated to give the title compound without further purification.
  • 33
  • [ 1199-47-9 ]
  • C23H24Cl2N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / dimethyl sulfoxide / 0.33 h / 85 °C / Microwave irradiation 2: potassium carbonate / toluene / 0.42 h / 40 °C / Microwave irradiation
  • 34
  • [ 1199-47-9 ]
  • [ 106-93-4 ]
  • C12H17NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In dimethyl sulfoxide at 85℃; for 0.333333h; Microwave irradiation; Synthesis of DMBB As shown in Scheme 1, o-aminophenol (15 mmol), K2CO3 (5 eq., 20 mmol), 1,2-dibromoethane (22 mmol), and DMSO (40 mL) were sequentially added to a 250 mL three-necked flask. The flask was put into the microwave catalytic synthesizer, and the reaction parameters were set as 1000 W, 85°C, and 20 min. The mixture was cooled to room temperature, filtered, extracted with EtOAc, and dried over anhydrous MgSO4. Solvent was removed, and the residue was purified by chromatography on a silica gel column with petroleum ether and EtOAc in a ratio of 6:1 (V/V) as eluant to obtain the compound 3. The substituted phenyl isoxazole formyl chloride (0.06 mol), compound 3 (0.05 mol), and anhydrous K2CO3 (5 eq., 0.38 g) were added in toluene (40 mL). Then, the reaction was carried out under the microwave condition (800 W, 40°C, and 25 min). The solution was cooled, filtered, and the organic phase was washed with water and dried over anhydrous Mg2SO4. Solvent was removed. The residue was purified on a silica gel column with the same eluant to obtain DMBB. White crystal, yield: 70 %, m.p. 178.6-179.4 °C. IR(KBr) v (cm-1): 3048-2902 (C-H), 1636 (C=O). 1H-NMR (400 MHz, CDCl3) δ (ppm): 7.44-6.82 (m, 6H, Ar-H),4.27-3.84 (m, 4H, O-CH2CH2-N), 2.18 (s, 3H, -CH3), 1.20 (s, 9H, -[CH3]3). 13C-NMR (100 MHz, CDCl3) δ (ppm): 169.81, 160.02, 158.90, 144.22, 143.66, 131.33, 130.26,128.31, 128.31, 127.05, 127.01, 124.70, 123.33, 120.25, 116.69, 113.04, 66.58, 41.76, 34.25, 31.36, 31.36, 31.36, 12.47. HRMS (ESI) calculated for C23H22Cl2N2O3 445.1080 ([M+H+]), found 445.1084.
  • 35
  • [ 1199-47-9 ]
  • C14H20N2O3 [ No CAS ]
  • C24H33N3O3*ClH [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: C14H20N2O3 With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 2-amino-5-(tert-butyl)phenol In N,N-dimethyl-formamide at 20℃; for 72h; Stage #3: With hydrogenchloride In methanol at 20℃; 2.2.2.3. N-(5-(tert-butyl)-2-hydroxyphenyl)-5-(4-(2-hydroxyphenyl)piperazin-1-yl)pentanamide hydrochloride (15) General procedure: To a solution of intermediate 6 (1 mmol) in 5 mL of DMF, 1,1'-carbonyldiimidazole (1.5 mmol) was added and the mixture was stirred at room temperature for 30 min. Then, 2-amino-4-(tert-butyl)phenol (1 mmol)was added and stirring was continued for 3 days. After that time, several drops of water were added and the reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography (DCM/MeOH 9:1, v/v). The free base after dissolving in 2 mL of MeOH was treated with 1 N solution of HCl(g) in MeOH to give compound 15 with yield of 66 %, Rf = 0.51; m.p. 222-224 °C; 1H NMR (300 MHz, DMSO-d6) δ ppm 1.20 (s, 9H), 1.55 - 1.68 (m, 2H), 1.68 - 1.84 (m, 2H), 2.45 (t, J = 7.03 Hz, 2H), 2.99 -3.19 (m, 6H), 3.41 - 3.54 (m, 4H), 6.69 - 6.90 (m, 5H), 6.95 (m, 1H), 7.70 (m, 1H), 9.31 (s, 1H), 9.44 (s, 1H), 9.57 (s, 1H), 10.44 (br.s.); 13C NMR (75 MHz, DMSO-d6) δ ppm 23.0, 23.3, 31.2, 31.9, 34.3, 35.7, 47.4, 51.8, 116.3, 116.3, 119.2, 119.9, 120.0, 122.1, 124.1, 124.1, 126.2, 141.8, 146.2, 150.6, 172.0; LC/MS: m/z calcd 426.33, found 426.20; MW 462.02; elemental analysis calcd (%) for C25H36ClN3O3: C 64.99, H 7.85, N 9.09; found: C 64.95, H 7.85, N 9.08.
  • 36
  • [ 1199-47-9 ]
  • 5-(4-(2-hydroxyphenyl)piperazin-1-yl)pentanoic acid [ No CAS ]
  • N-(5-(tert-butyl)-2-hydroxyphenyl)-5-(4-(2-hydroxyphenyl)piperazin-1-yl)pentanamide hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% Stage #1: 5-(4-(2-hydroxyphenyl)piperazin-1-yl)pentanoic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 2-amino-5-(tert-butyl)phenol In N,N-dimethyl-formamide at 20℃; for 72h; Stage #3: With hydrogenchloride In methanol at 20℃; 2.2.2.3. N-(5-(tert-butyl)-2-hydroxyphenyl)-5-(4-(2-hydroxyphenyl)piperazin-1-yl)pentanamide hydrochloride (15) To a solution of intermediate 6 (1 mmol) in 5 mL of DMF, 1,1'-carbonyldiimidazole (1.5 mmol) was added and the mixture was stirred at room temperature for 30 min. Then, 2-amino-4-(tert-butyl)phenol (1 mmol)was added and stirring was continued for 3 days. After that time, several drops of water were added and the reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography (DCM/MeOH 9:1, v/v). The free base after dissolving in 2 mL of MeOH was treated with 1 N solution of HCl(g) in MeOH to give compound 15 with yield of 66 %, Rf = 0.51; m.p. 222-224 °C; 1H NMR (300 MHz, DMSO-d6) δ ppm 1.20 (s, 9H), 1.55 - 1.68 (m, 2H), 1.68 - 1.84 (m, 2H), 2.45 (t, J = 7.03 Hz, 2H), 2.99 -3.19 (m, 6H), 3.41 - 3.54 (m, 4H), 6.69 - 6.90 (m, 5H), 6.95 (m, 1H), 7.70 (m, 1H), 9.31 (s, 1H), 9.44 (s, 1H), 9.57 (s, 1H), 10.44 (br.s.); 13C NMR (75 MHz, DMSO-d6) δ ppm 23.0, 23.3, 31.2, 31.9, 34.3, 35.7, 47.4, 51.8, 116.3, 116.3, 119.2, 119.9, 120.0, 122.1, 124.1, 124.1, 126.2, 141.8, 146.2, 150.6, 172.0; LC/MS: m/z calcd 426.33, found 426.20; MW 462.02; elemental analysis calcd (%) for C25H36ClN3O3: C 64.99, H 7.85, N 9.09; found: C 64.95, H 7.85, N 9.08.
  • 37
  • [ 1020001-25-5 ]
  • [ 1199-47-9 ]
  • C26H37N3O3*ClH [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: C16H24N2O3 With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 2-amino-5-(tert-butyl)phenol In N,N-dimethyl-formamide at 20℃; for 72h; Stage #3: With hydrogenchloride In methanol at 20℃; 2.2.2.3. N-(5-(tert-butyl)-2-hydroxyphenyl)-5-(4-(2-hydroxyphenyl)piperazin-1-yl)pentanamide hydrochloride (15) General procedure: To a solution of intermediate 6 (1 mmol) in 5 mL of DMF, 1,1'-carbonyldiimidazole (1.5 mmol) was added and the mixture was stirred at room temperature for 30 min. Then, 2-amino-4-(tert-butyl)phenol (1 mmol)was added and stirring was continued for 3 days. After that time, several drops of water were added and the reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography (DCM/MeOH 9:1, v/v). The free base after dissolving in 2 mL of MeOH was treated with 1 N solution of HCl(g) in MeOH to give compound 15 with yield of 66 %, Rf = 0.51; m.p. 222-224 °C; 1H NMR (300 MHz, DMSO-d6) δ ppm 1.20 (s, 9H), 1.55 - 1.68 (m, 2H), 1.68 - 1.84 (m, 2H), 2.45 (t, J = 7.03 Hz, 2H), 2.99 -3.19 (m, 6H), 3.41 - 3.54 (m, 4H), 6.69 - 6.90 (m, 5H), 6.95 (m, 1H), 7.70 (m, 1H), 9.31 (s, 1H), 9.44 (s, 1H), 9.57 (s, 1H), 10.44 (br.s.); 13C NMR (75 MHz, DMSO-d6) δ ppm 23.0, 23.3, 31.2, 31.9, 34.3, 35.7, 47.4, 51.8, 116.3, 116.3, 119.2, 119.9, 120.0, 122.1, 124.1, 124.1, 126.2, 141.8, 146.2, 150.6, 172.0; LC/MS: m/z calcd 426.33, found 426.20; MW 462.02; elemental analysis calcd (%) for C25H36ClN3O3: C 64.99, H 7.85, N 9.09; found: C 64.95, H 7.85, N 9.08.
  • 38
  • [ 1199-47-9 ]
  • C17H26N2O3 [ No CAS ]
  • C27H39N3O3*ClH [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: C17H26N2O3 With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 2-amino-5-(tert-butyl)phenol In N,N-dimethyl-formamide at 20℃; for 72h; Stage #3: With hydrogenchloride In methanol at 20℃; 2.2.2.3. N-(5-(tert-butyl)-2-hydroxyphenyl)-5-(4-(2-hydroxyphenyl)piperazin-1-yl)pentanamide hydrochloride (15) General procedure: To a solution of intermediate 6 (1 mmol) in 5 mL of DMF, 1,1'-carbonyldiimidazole (1.5 mmol) was added and the mixture was stirred at room temperature for 30 min. Then, 2-amino-4-(tert-butyl)phenol (1 mmol)was added and stirring was continued for 3 days. After that time, several drops of water were added and the reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography (DCM/MeOH 9:1, v/v). The free base after dissolving in 2 mL of MeOH was treated with 1 N solution of HCl(g) in MeOH to give compound 15 with yield of 66 %, Rf = 0.51; m.p. 222-224 °C; 1H NMR (300 MHz, DMSO-d6) δ ppm 1.20 (s, 9H), 1.55 - 1.68 (m, 2H), 1.68 - 1.84 (m, 2H), 2.45 (t, J = 7.03 Hz, 2H), 2.99 -3.19 (m, 6H), 3.41 - 3.54 (m, 4H), 6.69 - 6.90 (m, 5H), 6.95 (m, 1H), 7.70 (m, 1H), 9.31 (s, 1H), 9.44 (s, 1H), 9.57 (s, 1H), 10.44 (br.s.); 13C NMR (75 MHz, DMSO-d6) δ ppm 23.0, 23.3, 31.2, 31.9, 34.3, 35.7, 47.4, 51.8, 116.3, 116.3, 119.2, 119.9, 120.0, 122.1, 124.1, 124.1, 126.2, 141.8, 146.2, 150.6, 172.0; LC/MS: m/z calcd 426.33, found 426.20; MW 462.02; elemental analysis calcd (%) for C25H36ClN3O3: C 64.99, H 7.85, N 9.09; found: C 64.95, H 7.85, N 9.08.
  • 39
  • [ 1199-47-9 ]
  • [ 98-59-9 ]
  • C17H21NO3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine In dichloromethane at 0 - 20℃; for 12.1667h;
  • 40
  • [ 1199-47-9 ]
  • 7-(tert-butyl)-4-tosyl-2-vinyl-3,4-dihydro-2H-benzo[b][1,4]oxazine [ No CAS ]
  • (R)-7-(tert-butyl)-4-tosyl-2-vinyl-3,4-dihydro-2H-benzo[b][1,4]oxazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: pyridine / dichloromethane / 12.17 h / 0 - 20 °C 2: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 24 h / 0 - 20 °C 3: palladium diacetate; biphenyl-4-carboxylic acid; C15H14N2O / toluene / 24 h / 50 °C / Sealed tube
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