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[ CAS No. 61832-41-5 ] {[proInfo.proName]}

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Product Details of [ 61832-41-5 ]

CAS No. :61832-41-5 MDL No. :MFCD00040994
Formula : C4H8N2O2S Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 148.18 Pubchem ID :-
Synonyms :
Chemical Name :N-Methyl-1-(methylthio)-2-nitroethenamine

Safety of [ 61832-41-5 ]

Signal Word:Danger Class:9
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P310-P362+P364-P403+P233-P501 UN#:3335
Hazard Statements:H315-H318-H335-H411 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 61832-41-5 ]

* 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 [ 61832-41-5 ]

[ 61832-41-5 ] Synthesis Path-Downstream   1~39

  • 1
  • [ 102721-76-6 ]
  • [ 78441-62-0 ]
  • [ 76963-41-2 ]
YieldReaction ConditionsOperation in experiment
81.0% In water; at 20 - 35℃; for 8h; N-METHYL-L-METHYLTHIO-2-NITROETHYLENEAMINE (NMSM, 610 g; 4.12 mol) is mixed with water (1500 ml), and the mixture is cool to 20-25 C. 4- (2-Aminoethyl) DIIOMETHYL-2-DIMETHYLAMINOMETHYLTHIAZOLE (1000 g; 4.32 mol) dissolved in water (1500 ML) is added into this suspension at 20-25 C. The reaction mixture is warmed to 30-35° C and continued the reaction for 8 h. The progress of the reaction is monitored by qualitative HPLC analysis. The reaction mixture is extracted with toluene (2 x 1000 ml), and the aqueous layer is treated with activated carbon (50 g) at 55-60 C for 30 min. Activated carbon is removed by filtration through HYFLO bed and the aqueous filtrate is extracted with chloroform (4 x 1000 I THE CHLOROFORM extract is concentrated under reduced pressure at less than 50 C ; ethyl acetate (3000 ML) is added into the concentrate and reconcentrated. Acetone (300 ml), ethyl acetate (300 ML) is added into the concentrate and cooled to 0-5 C to crystallize the product. The product is filtered, washed with precooled ethyl acetate (250 ml), and dried to obtain pure Nizatidine 1160 g. Yield = 81.0percent ; HPLC purity ~ 99.3percent.
80.6% In water; at 30℃; Weigh 102g of 2- (dimethylaminomethyl) -4- (2-aminoethylthiomethyl) thiazole64.3 g of N-methyl-1-methylthio-2-nitroethylene amine,mixing,Add 306mL of water,At 30 ° C until the reaction of the starting material is complete,Then add 10g activated carbon bleaching,Suction filtration,Finally, add 400mL of anhydrous ethanol for recrystallization,The recrystallization process is:The material obtained by suction filtration was added to absolute ethanol,Begin to heat up to 70 ,Then heat to solid all dissolved,Then slowly cooled to 0-5 ,Insulation 6h,Finally centrifugedNizatidineThe yield of this process is 80.6percentPurity 99.7percent.
  • 2
  • [ 700-44-7 ]
  • [ 61832-41-5 ]
  • [ 1173429-46-3 ]
YieldReaction ConditionsOperation in experiment
89% Stage #1: 6-methoxysalicylaldehyde With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol at 20℃; Stage #2: (E-)-N-methyl-1-(methylthio)-2-nitroethanamine In methanol at 20℃; for 12h;
  • 3
  • [ 613-84-3 ]
  • [ 61832-41-5 ]
  • [ 916850-57-2 ]
YieldReaction ConditionsOperation in experiment
94% With cholin hydroxide In water at 20℃; for 5h; Green chemistry; Synthesis of N-Methyl-4-(methylthio)-3-nitro-4Hchromen-2-amine (3a) General procedure: The ChOH 10 mol% in water (3 mL) was added to a mixture of 2-hydroxybenzaldehyde (1a, 1.0 mmol) and (E)-N-methyl-1-(methylthio)-2-nitroethenamine (2, 1.0 mmol) (1 mmol) in a 10mL reaction flask equipped with a magnetic stirrer. The resulting mixture was stirred for the appropriate time at room temperature. After completion of the reaction (confirmed by TLC, hexanes: EtOAc 1:1), the solid product was filtered and washed with water. The obtained crude product was recrystallized from ethanol to yield the pure product. The same method was adopted for the synthesis of all the targeted products 3a-x.
88% Stage #1: 2-hydroxy-5-methylbenzaldehyde With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol at 20℃; Stage #2: (E-)-N-methyl-1-(methylthio)-2-nitroethanamine In methanol at 20℃; for 15h;
  • 4
  • [ 61832-41-5 ]
  • [ 34333-12-5 ]
  • [ 1173429-59-8 ]
  • 5
  • [ 61832-41-5 ]
  • [ 52085-14-0 ]
  • [ 1173429-61-2 ]
YieldReaction ConditionsOperation in experiment
90% With cholin hydroxide; In water; at 20℃; for 5h;Green chemistry; General procedure: The ChOH 10 mol% in water (3 mL) was added to a mixture of 2-hydroxybenzaldehyde (1a, 1.0 mmol) and (E)-N-methyl-1-(methylthio)-2-nitroethenamine (2, 1.0 mmol) (1 mmol) in a 10mL reaction flask equipped with a magnetic stirrer. The resulting mixture was stirred for the appropriate time at room temperature. After completion of the reaction (confirmed by TLC, hexanes: EtOAc 1:1), the solid product was filtered and washed with water. The obtained crude product was recrystallized from ethanol to yield the pure product. The same method was adopted for the synthesis of all the targeted products 3a-x.
  • 6
  • [ 18278-34-7 ]
  • [ 61832-41-5 ]
  • [ 1620024-47-6 ]
YieldReaction ConditionsOperation in experiment
90% With toluene-4-sulfonic acid In water at 20℃; for 0.25h; Green chemistry; 4.1.1. General procedure for the synthesis of multi-substituted 1,4-DHPs (6a-u) General procedure: A mixture of solution containing aldehyde (1.0 equiv), NMSM (2.0equiv) and PTSA (0.1 equiv) in water (3 mL) was stirred at room temperaturefor about 15 min. The solid formation observed. The TLC withmobile phase of hexane: EtOAc mixture has been used to monitor thecompletion of the reaction. The resulted solid was cooled to 0-5 C andfiltered under vaccum. The crude products were recrystallized fromdichloromethane and hexane mixture (9:1) to obtain analytically pureproducts (6a-u). The spectral characterisation data and spectra areincluded in the supporting information.
82% With 2-aminopyridine In ethanol at 80℃; for 15h;
  • 7
  • [ 61832-41-5 ]
  • [ 21487-45-6 ]
  • [ 1620024-53-4 ]
YieldReaction ConditionsOperation in experiment
80% With toluene-4-sulfonic acid In water at 20℃; for 0.25h; Green chemistry; 4.1.1. General procedure for the synthesis of multi-substituted 1,4-DHPs (6a-u) General procedure: A mixture of solution containing aldehyde (1.0 equiv), NMSM (2.0equiv) and PTSA (0.1 equiv) in water (3 mL) was stirred at room temperaturefor about 15 min. The solid formation observed. The TLC withmobile phase of hexane: EtOAc mixture has been used to monitor thecompletion of the reaction. The resulted solid was cooled to 0-5 C andfiltered under vaccum. The crude products were recrystallized fromdichloromethane and hexane mixture (9:1) to obtain analytically pureproducts (6a-u). The spectral characterisation data and spectra areincluded in the supporting information.
78% With 2-aminopyridine In ethanol at 80℃; for 12h;
  • 8
  • [ 61832-41-5 ]
  • [ 613-45-6 ]
  • [ 1620024-46-5 ]
YieldReaction ConditionsOperation in experiment
90% With toluene-4-sulfonic acid In water at 20℃; for 0.25h; Green chemistry; 4.1.1. General procedure for the synthesis of multi-substituted 1,4-DHPs (6a-u) General procedure: A mixture of solution containing aldehyde (1.0 equiv), NMSM (2.0equiv) and PTSA (0.1 equiv) in water (3 mL) was stirred at room temperaturefor about 15 min. The solid formation observed. The TLC withmobile phase of hexane: EtOAc mixture has been used to monitor thecompletion of the reaction. The resulted solid was cooled to 0-5 C andfiltered under vaccum. The crude products were recrystallized fromdichloromethane and hexane mixture (9:1) to obtain analytically pureproducts (6a-u). The spectral characterisation data and spectra areincluded in the supporting information.
88% With 2-aminopyridine In ethanol at 80℃; for 5h;
  • 9
  • [ 4230-93-7 ]
  • [ 61832-41-5 ]
  • 4-(3,4-dimethoxyphenyl)-1-methyl-2-(methylthio)-3-nitro-1H-pyrrole [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With iodine In neat (no solvent) at 55℃; for 0.0833333h; Green chemistry;
  • 10
  • [ 399-25-7 ]
  • [ 61832-41-5 ]
  • 4-(2-fluorophenyl)-1-methyl-2-(methylthio)-3-nitro-1H-pyrrole [ No CAS ]
  • 11
  • [ 1076-38-6 ]
  • [ 64622-16-8 ]
  • [ 61832-41-5 ]
  • 4-(2-Bromo-6-chlorophenyl)-2-(methylamino)-3-nitro-4H,5H-pyrano[3,2-c]chromen-5-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With silica-supported tungstic acid; at 80℃; for 0.616667h;Green chemistry; A mixture of 4-hydroxycoumarin (1, 1 mmol), 4-methoxybenzaldehyde (2a, 1 mmol), (E)-N-methyl-1-(methylthio)-2-nitroethenamine (3, 1 mmol) and silica-supported tungstic acid (STA) (10 mol %) was stirred at 80 C under solvent-free conditions. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was washed with ethanol. The residue dissolved in DCM, and the insoluble STA was separated by simple filtration and washed with DCM. The solvent was evaporated under reduced pressure and the obtained crude was recrystallized from ethanol to afford the pure yellow product 4a. The recovered catalyst was washed with ethyl acetate and acetone, dried and reused. Compounds 4b-4z were also synthesized by adopting this procedure.
  • 12
  • [ 61832-41-5 ]
  • [ 14580-22-4 ]
  • [ 82-86-0 ]
  • 1'-(2-chlorophenyl)-3'-methyl-6'-(methylamino)-5'-nitro-1'H,2H-spiro[acenaphthylene-1,4'-pyrano[2,3-c]pyrazol]-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% In ethanol for 3.5h; Reflux; chemoselective reaction; Typical procedure for preparation of 5a A mixture of acenaphthoquinone 1 (0.182 g, 1 mmol), 2-(2-chlorophenyl)-5-methyl-2,4-dihydro-3H-pyrazol-3-one 2 (0.208 g, 1 mmol) and (E)-N-methyl-1-(methylthio)-2-nitroethenamine 3 in EtOH (5 mL) was heated at reflux for 3.5 h. The progress of the reaction was monitored by TLC using EtOAc/n-hexane (1:1) as eluent. After completion of the reaction, the solid was washed with ethanol (95%, 5 mL) to obtain the product 5a in 83% yield. The product 5a was crystallized from ethanol for elemental analysis data.
  • 13
  • [ 86-79-3 ]
  • [ 61832-41-5 ]
  • [ 105-07-7 ]
  • 4-[3-(methylamino)-2-nitro-1,11-dihydropyrano[3,2-a]-carbazol-1-yl]benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% In neat (no solvent); at 150℃; for 0.0833333h;Microwave irradiation; General procedure: An oven-dried 10-ml microwave reaction vessel containing a stir bar was charged with 4-hydroxycarbazole (6)(0.183 g, 1 mmol) or <strong>[86-79-3]2-hydroxycarbazole</strong> (10) (0.183 g,1 mmol), the appropriate aromatic aldehyde 7a-k (1 mmol), and (E)-N-methyl-1-(methylsulfanyl)-2-nitroethenamine (8)(0.148 g, 1 mmol). The vessel was sealed with a plastic microwave septum. The vessel was placed into the CEM DiscoverSP system and the reaction was performed under the following conditions: 1-2 min ramp time, prestirring 30 s, stirring was set high. The maximum power and maximum pressure were set to 360 W and 250 psi, respectively, at 150C temperature for 5 min (hold time). After the microwave irradiation was completed, the mixture was cooled to room temperature and diluted with EtOH (10 ml). The precipitated solids were filtered off, washed with EtOH (5 ml), and dried to afford the pure products 9a-j or 11a-f
  • 14
  • [ 86-79-3 ]
  • [ 61832-41-5 ]
  • [ 591-31-1 ]
  • 1-(3-methoxyphenyl)-N-methyl-2-nitro-1,11-dihydropyrano[3,2-a]carbazol-3-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% In neat (no solvent); at 150℃; for 0.0833333h;Microwave irradiation; General procedure: An oven-dried 10-ml microwave reaction vessel containing a stir bar was charged with 4-hydroxycarbazole (6)(0.183 g, 1 mmol) or <strong>[86-79-3]2-hydroxycarbazole</strong> (10) (0.183 g,1 mmol), the appropriate aromatic aldehyde 7a-k (1 mmol), and (E)-N-methyl-1-(methylsulfanyl)-2-nitroethenamine (8)(0.148 g, 1 mmol). The vessel was sealed with a plastic microwave septum. The vessel was placed into the CEM DiscoverSP system and the reaction was performed under the following conditions: 1-2 min ramp time, prestirring 30 s, stirring was set high. The maximum power and maximum pressure were set to 360 W and 250 psi, respectively, at 150C temperature for 5 min (hold time). After the microwave irradiation was completed, the mixture was cooled to room temperature and diluted with EtOH (10 ml). The precipitated solids were filtered off, washed with EtOH (5 ml), and dried to afford the pure products 9a-j or 11a-f
  • 15
  • [ 500-22-1 ]
  • [ 86-79-3 ]
  • [ 61832-41-5 ]
  • N-methyl-2-nitro-1-(pyridin-3-yl)-1,11-dihydropyrano-[3,2-a]carbazol-3-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% In neat (no solvent); at 150℃; for 0.0833333h;Microwave irradiation; General procedure: An oven-dried 10-ml microwave reaction vessel containing a stir bar was charged with 4-hydroxycarbazole (6)(0.183 g, 1 mmol) or <strong>[86-79-3]2-hydroxycarbazole</strong> (10) (0.183 g,1 mmol), the appropriate aromatic aldehyde 7a-k (1 mmol), and (E)-N-methyl-1-(methylsulfanyl)-2-nitroethenamine (8)(0.148 g, 1 mmol). The vessel was sealed with a plastic microwave septum. The vessel was placed into the CEM DiscoverSP system and the reaction was performed under the following conditions: 1-2 min ramp time, prestirring 30 s, stirring was set high. The maximum power and maximum pressure were set to 360 W and 250 psi, respectively, at 150C temperature for 5 min (hold time). After the microwave irradiation was completed, the mixture was cooled to room temperature and diluted with EtOH (10 ml). The precipitated solids were filtered off, washed with EtOH (5 ml), and dried to afford the pure products 9a-j or 11a-f
  • 16
  • [ 86-79-3 ]
  • [ 61832-41-5 ]
  • [ 1122-91-4 ]
  • 1-(4-bromophenyl)-N-methyl-2-nitro-1,11-dihydropyrano[3,2-a]carbazol-3-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% In neat (no solvent); at 150℃; for 0.0833333h;Microwave irradiation; General procedure: An oven-dried 10-ml microwave reaction vessel containing a stir bar was charged with 4-hydroxycarbazole (6)(0.183 g, 1 mmol) or <strong>[86-79-3]2-hydroxycarbazole</strong> (10) (0.183 g,1 mmol), the appropriate aromatic aldehyde 7a-k (1 mmol), and (E)-N-methyl-1-(methylsulfanyl)-2-nitroethenamine (8)(0.148 g, 1 mmol). The vessel was sealed with a plastic microwave septum. The vessel was placed into the CEM DiscoverSP system and the reaction was performed under the following conditions: 1-2 min ramp time, prestirring 30 s, stirring was set high. The maximum power and maximum pressure were set to 360 W and 250 psi, respectively, at 150C temperature for 5 min (hold time). After the microwave irradiation was completed, the mixture was cooled to room temperature and diluted with EtOH (10 ml). The precipitated solids were filtered off, washed with EtOH (5 ml), and dried to afford the pure products 9a-j or 11a-f
  • 17
  • [ 86-79-3 ]
  • [ 61832-41-5 ]
  • [ 555-16-8 ]
  • N-methyl-2-nitro-1-(4-nitrophenyl)-1,11-dihydropyrano-[3,2-a]carbazol-3-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% In neat (no solvent); at 150℃; for 0.0833333h;Microwave irradiation; General procedure: An oven-dried 10-ml microwave reaction vessel containing a stir bar was charged with 4-hydroxycarbazole (6)(0.183 g, 1 mmol) or <strong>[86-79-3]2-hydroxycarbazole</strong> (10) (0.183 g,1 mmol), the appropriate aromatic aldehyde 7a-k (1 mmol), and (E)-N-methyl-1-(methylsulfanyl)-2-nitroethenamine (8)(0.148 g, 1 mmol). The vessel was sealed with a plastic microwave septum. The vessel was placed into the CEM DiscoverSP system and the reaction was performed under the following conditions: 1-2 min ramp time, prestirring 30 s, stirring was set high. The maximum power and maximum pressure were set to 360 W and 250 psi, respectively, at 150C temperature for 5 min (hold time). After the microwave irradiation was completed, the mixture was cooled to room temperature and diluted with EtOH (10 ml). The precipitated solids were filtered off, washed with EtOH (5 ml), and dried to afford the pure products 9a-j or 11a-f
  • 18
  • [ 86-79-3 ]
  • [ 61832-41-5 ]
  • [ 100-52-7 ]
  • N-methyl-2-nitro-1-phenyl-1,11-dihydropyrano[3,2-a]-carbazol-3-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% In neat (no solvent); at 150℃; for 0.0833333h;Microwave irradiation; General procedure: An oven-dried 10-ml microwave reaction vessel containing a stir bar was charged with 4-hydroxycarbazole (6)(0.183 g, 1 mmol) or <strong>[86-79-3]2-hydroxycarbazole</strong> (10) (0.183 g,1 mmol), the appropriate aromatic aldehyde 7a-k (1 mmol), and (E)-N-methyl-1-(methylsulfanyl)-2-nitroethenamine (8)(0.148 g, 1 mmol). The vessel was sealed with a plastic microwave septum. The vessel was placed into the CEM DiscoverSP system and the reaction was performed under the following conditions: 1-2 min ramp time, prestirring 30 s, stirring was set high. The maximum power and maximum pressure were set to 360 W and 250 psi, respectively, at 150C temperature for 5 min (hold time). After the microwave irradiation was completed, the mixture was cooled to room temperature and diluted with EtOH (10 ml). The precipitated solids were filtered off, washed with EtOH (5 ml), and dried to afford the pure products 9a-j or 11a-f
  • 19
  • [ 43057-77-8 ]
  • [ 61832-41-5 ]
  • 7-ethoxy-N-methyl-4-(methylthio)-3-nitro-4H-chromen-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With cholin hydroxide; In water; at 20℃; for 5.3h;Green chemistry; General procedure: The ChOH 10 mol% in water (3 mL) was added to a mixture of 2-hydroxybenzaldehyde (1a, 1.0 mmol) and (E)-N-methyl-1-(methylthio)-2-nitroethenamine (2, 1.0 mmol) (1 mmol) in a 10mL reaction flask equipped with a magnetic stirrer. The resulting mixture was stirred for the appropriate time at room temperature. After completion of the reaction (confirmed by TLC, hexanes: EtOAc 1:1), the solid product was filtered and washed with water. The obtained crude product was recrystallized from ethanol to yield the pure product. The same method was adopted for the synthesis of all the targeted products 3a-x.
  • 20
  • [ 492-88-6 ]
  • [ 61832-41-5 ]
  • 8-ethoxy-N-methyl-4-(methylthio)-3-nitro-4H-chromen-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With cholin hydroxide In water at 20℃; for 5h; Green chemistry; Synthesis of N-Methyl-4-(methylthio)-3-nitro-4Hchromen-2-amine (3a) General procedure: The ChOH 10 mol% in water (3 mL) was added to a mixture of 2-hydroxybenzaldehyde (1a, 1.0 mmol) and (E)-N-methyl-1-(methylthio)-2-nitroethenamine (2, 1.0 mmol) (1 mmol) in a 10mL reaction flask equipped with a magnetic stirrer. The resulting mixture was stirred for the appropriate time at room temperature. After completion of the reaction (confirmed by TLC, hexanes: EtOAc 1:1), the solid product was filtered and washed with water. The obtained crude product was recrystallized from ethanol to yield the pure product. The same method was adopted for the synthesis of all the targeted products 3a-x.
  • 21
  • [ 19652-32-5 ]
  • [ 61832-41-5 ]
  • 8-bromo-6-chloro-N-methyl-4-(methylthio)-3-nitro-4H-chromen-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With cholin hydroxide; In water; at 20℃; for 6h;Green chemistry; General procedure: The ChOH 10 mol% in water (3 mL) was added to a mixture of 2-hydroxybenzaldehyde (1a, 1.0 mmol) and (E)-N-methyl-1-(methylthio)-2-nitroethenamine (2, 1.0 mmol) (1 mmol) in a 10mL reaction flask equipped with a magnetic stirrer. The resulting mixture was stirred for the appropriate time at room temperature. After completion of the reaction (confirmed by TLC, hexanes: EtOAc 1:1), the solid product was filtered and washed with water. The obtained crude product was recrystallized from ethanol to yield the pure product. The same method was adopted for the synthesis of all the targeted products 3a-x.
  • 22
  • [ 37942-07-7 ]
  • [ 61832-41-5 ]
  • 6,8-di-tert-butyl-N-methyl-4-(methylthio)-3-nitro-4H-chromen-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With cholin hydroxide In water at 20℃; for 5h; Green chemistry; Synthesis of N-Methyl-4-(methylthio)-3-nitro-4Hchromen-2-amine (3a) General procedure: The ChOH 10 mol% in water (3 mL) was added to a mixture of 2-hydroxybenzaldehyde (1a, 1.0 mmol) and (E)-N-methyl-1-(methylthio)-2-nitroethenamine (2, 1.0 mmol) (1 mmol) in a 10mL reaction flask equipped with a magnetic stirrer. The resulting mixture was stirred for the appropriate time at room temperature. After completion of the reaction (confirmed by TLC, hexanes: EtOAc 1:1), the solid product was filtered and washed with water. The obtained crude product was recrystallized from ethanol to yield the pure product. The same method was adopted for the synthesis of all the targeted products 3a-x.
  • 23
  • [ 939-97-9 ]
  • [ 61832-41-5 ]
  • [ 90908-89-7 ]
  • 4-(4-tert-butylphenyl)-6-(methylamino)-5-nitro-2-(1H-pyrrol-2-yl)-4H-pyran-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With piperidine In ethanol at 90℃; for 0.25h; Sealed tube; Microwave irradiation; 4-Aryl-6-(methylamino)-5-nitro-2-(1H-pyrrol-2-yl)-4H-pyran-3-carbonitriles 4a-4o (general procedure).a. Microwave-assisted synthesis. General procedure: A 30-mL microwaveglass vial was charged with 0.2 g (1.0 mmol)of 3-oxo-3-(1H-pyrrol-2-yl)propanenitrile (1), 1.0 mmol of aromatic aldehyde 3a-3o, 0.12 g(1.0 mmol) of (E)-N-methyl-1-(methylsulfanyl)-2-nitroethenamine (2), and a catalytic amount of piperidinein 10 mL of ethanol. The vial was sealed, placedin a microwave chamber, and irradiated at 90°C withstirring for 15-20 min. After completion of the reaction(TLC), the mixture was cooled to room temperatureand poured into ice-cold water (20 mL), and theprecipitate was filtered off, washed with cold ethanol(5-7 mL), and dried.
  • 24
  • [ 61832-41-5 ]
  • [ 1122-91-4 ]
  • [ 90908-89-7 ]
  • 4-(4-bromophenyl)-6-(methylamino)-5-nitro-2-(1H-pyrrol-2-yl)-4H-pyran-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With piperidine In ethanol at 90℃; for 0.25h; Sealed tube; Microwave irradiation; 4-Aryl-6-(methylamino)-5-nitro-2-(1H-pyrrol-2-yl)-4H-pyran-3-carbonitriles 4a-4o (general procedure).a. Microwave-assisted synthesis. General procedure: A 30-mL microwaveglass vial was charged with 0.2 g (1.0 mmol)of 3-oxo-3-(1H-pyrrol-2-yl)propanenitrile (1), 1.0 mmol of aromatic aldehyde 3a-3o, 0.12 g(1.0 mmol) of (E)-N-methyl-1-(methylsulfanyl)-2-nitroethenamine (2), and a catalytic amount of piperidinein 10 mL of ethanol. The vial was sealed, placedin a microwave chamber, and irradiated at 90°C withstirring for 15-20 min. After completion of the reaction(TLC), the mixture was cooled to room temperatureand poured into ice-cold water (20 mL), and theprecipitate was filtered off, washed with cold ethanol(5-7 mL), and dried.
  • 25
  • [ 61832-41-5 ]
  • [ 459-57-4 ]
  • [ 90908-89-7 ]
  • 4-(4-fluorophenyl)-6-(methylamino)-5-nitro-2-(1H-pyrrol-2-yl)-4H-pyran-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With piperidine In ethanol at 90℃; for 0.333333h; Sealed tube; Microwave irradiation; 4-Aryl-6-(methylamino)-5-nitro-2-(1H-pyrrol-2-yl)-4H-pyran-3-carbonitriles 4a-4o (general procedure).a. Microwave-assisted synthesis. General procedure: A 30-mL microwaveglass vial was charged with 0.2 g (1.0 mmol)of 3-oxo-3-(1H-pyrrol-2-yl)propanenitrile (1), 1.0 mmol of aromatic aldehyde 3a-3o, 0.12 g(1.0 mmol) of (E)-N-methyl-1-(methylsulfanyl)-2-nitroethenamine (2), and a catalytic amount of piperidinein 10 mL of ethanol. The vial was sealed, placedin a microwave chamber, and irradiated at 90°C withstirring for 15-20 min. After completion of the reaction(TLC), the mixture was cooled to room temperatureand poured into ice-cold water (20 mL), and theprecipitate was filtered off, washed with cold ethanol(5-7 mL), and dried.
  • 26
  • [ 3132-99-8 ]
  • [ 61832-41-5 ]
  • [ 90908-89-7 ]
  • 4-(3-bromophenyl)-6-(methylamino)-5-nitro-2-(1H-pyrrol-2-yl)-4H-pyran-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With piperidine In ethanol at 90℃; for 0.333333h; Sealed tube; Microwave irradiation; 4-Aryl-6-(methylamino)-5-nitro-2-(1H-pyrrol-2-yl)-4H-pyran-3-carbonitriles 4a-4o (general procedure).a. Microwave-assisted synthesis. General procedure: A 30-mL microwaveglass vial was charged with 0.2 g (1.0 mmol)of 3-oxo-3-(1H-pyrrol-2-yl)propanenitrile (1), 1.0 mmol of aromatic aldehyde 3a-3o, 0.12 g(1.0 mmol) of (E)-N-methyl-1-(methylsulfanyl)-2-nitroethenamine (2), and a catalytic amount of piperidinein 10 mL of ethanol. The vial was sealed, placedin a microwave chamber, and irradiated at 90°C withstirring for 15-20 min. After completion of the reaction(TLC), the mixture was cooled to room temperatureand poured into ice-cold water (20 mL), and theprecipitate was filtered off, washed with cold ethanol(5-7 mL), and dried.
  • 27
  • [ 61832-41-5 ]
  • [ 58551-83-0 ]
  • [ 90908-89-7 ]
  • 6-(methylamino)-5-nitro-2-(1H-pyrrol-2-yl)-4-(2,4,6-trifluorophenyl)-4H-pyran-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With piperidine In ethanol at 90℃; for 0.333333h; Sealed tube; Microwave irradiation; 4-Aryl-6-(methylamino)-5-nitro-2-(1H-pyrrol-2-yl)-4H-pyran-3-carbonitriles 4a-4o (general procedure).a. Microwave-assisted synthesis. General procedure: A 30-mL microwaveglass vial was charged with 0.2 g (1.0 mmol)of 3-oxo-3-(1H-pyrrol-2-yl)propanenitrile (1), 1.0 mmol of aromatic aldehyde 3a-3o, 0.12 g(1.0 mmol) of (E)-N-methyl-1-(methylsulfanyl)-2-nitroethenamine (2), and a catalytic amount of piperidinein 10 mL of ethanol. The vial was sealed, placedin a microwave chamber, and irradiated at 90°C withstirring for 15-20 min. After completion of the reaction(TLC), the mixture was cooled to room temperatureand poured into ice-cold water (20 mL), and theprecipitate was filtered off, washed with cold ethanol(5-7 mL), and dried.
  • 28
  • [ 61832-41-5 ]
  • [ 6334-18-5 ]
  • [ 90908-89-7 ]
  • 4-(2,3-dichlorophenyl)-6-(methylamino)-5-nitro-2-(1H-pyrrol-2-yl)-4H-pyran-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With piperidine In ethanol at 90℃; for 0.333333h; Sealed tube; Microwave irradiation; 4-Aryl-6-(methylamino)-5-nitro-2-(1H-pyrrol-2-yl)-4H-pyran-3-carbonitriles 4a-4o (general procedure).a. Microwave-assisted synthesis. General procedure: A 30-mL microwaveglass vial was charged with 0.2 g (1.0 mmol)of 3-oxo-3-(1H-pyrrol-2-yl)propanenitrile (1), 1.0 mmol of aromatic aldehyde 3a-3o, 0.12 g(1.0 mmol) of (E)-N-methyl-1-(methylsulfanyl)-2-nitroethenamine (2), and a catalytic amount of piperidinein 10 mL of ethanol. The vial was sealed, placedin a microwave chamber, and irradiated at 90°C withstirring for 15-20 min. After completion of the reaction(TLC), the mixture was cooled to room temperatureand poured into ice-cold water (20 mL), and theprecipitate was filtered off, washed with cold ethanol(5-7 mL), and dried.
  • 29
  • [ 61832-41-5 ]
  • [ 100-52-7 ]
  • [ 90908-89-7 ]
  • 6-(methylamino)-5-nitro-4-phenyl-2-(1H-pyrrol-2-yl)-4H-pyran-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With piperidine In ethanol at 90℃; for 0.333333h; Sealed tube; Microwave irradiation; 4-Aryl-6-(methylamino)-5-nitro-2-(1H-pyrrol-2-yl)-4H-pyran-3-carbonitriles 4a-4o (general procedure).a. Microwave-assisted synthesis. General procedure: A 30-mL microwaveglass vial was charged with 0.2 g (1.0 mmol)of 3-oxo-3-(1H-pyrrol-2-yl)propanenitrile (1), 1.0 mmol of aromatic aldehyde 3a-3o, 0.12 g(1.0 mmol) of (E)-N-methyl-1-(methylsulfanyl)-2-nitroethenamine (2), and a catalytic amount of piperidinein 10 mL of ethanol. The vial was sealed, placedin a microwave chamber, and irradiated at 90°C withstirring for 15-20 min. After completion of the reaction(TLC), the mixture was cooled to room temperatureand poured into ice-cold water (20 mL), and theprecipitate was filtered off, washed with cold ethanol(5-7 mL), and dried.
  • 30
  • [ 61832-41-5 ]
  • [ 123-08-0 ]
  • [ 90908-89-7 ]
  • 4-(4-hydroxyphenyl)-6-(methylamino)-5-nitro-2-(1H-pyrrol-2-yl)-4H-pyran-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With piperidine In ethanol at 90℃; for 0.25h; Sealed tube; Microwave irradiation; 4-Aryl-6-(methylamino)-5-nitro-2-(1H-pyrrol-2-yl)-4H-pyran-3-carbonitriles 4a-4o (general procedure).a. Microwave-assisted synthesis. General procedure: A 30-mL microwaveglass vial was charged with 0.2 g (1.0 mmol)of 3-oxo-3-(1H-pyrrol-2-yl)propanenitrile (1), 1.0 mmol of aromatic aldehyde 3a-3o, 0.12 g(1.0 mmol) of (E)-N-methyl-1-(methylsulfanyl)-2-nitroethenamine (2), and a catalytic amount of piperidinein 10 mL of ethanol. The vial was sealed, placedin a microwave chamber, and irradiated at 90°C withstirring for 15-20 min. After completion of the reaction(TLC), the mixture was cooled to room temperatureand poured into ice-cold water (20 mL), and theprecipitate was filtered off, washed with cold ethanol(5-7 mL), and dried.
  • 31
  • [ 61832-41-5 ]
  • [ 450-83-9 ]
  • [ 90908-89-7 ]
  • 4-(4-fluoro-2-methoxyphenyl)-6-(methylamino)-5-nitro-2-(1H-pyrrol-2-yl)-4H-pyran-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With piperidine In ethanol at 90℃; for 0.333333h; Sealed tube; Microwave irradiation; 4-Aryl-6-(methylamino)-5-nitro-2-(1H-pyrrol-2-yl)-4H-pyran-3-carbonitriles 4a-4o (general procedure).a. Microwave-assisted synthesis. General procedure: A 30-mL microwaveglass vial was charged with 0.2 g (1.0 mmol)of 3-oxo-3-(1H-pyrrol-2-yl)propanenitrile (1), 1.0 mmol of aromatic aldehyde 3a-3o, 0.12 g(1.0 mmol) of (E)-N-methyl-1-(methylsulfanyl)-2-nitroethenamine (2), and a catalytic amount of piperidinein 10 mL of ethanol. The vial was sealed, placedin a microwave chamber, and irradiated at 90°C withstirring for 15-20 min. After completion of the reaction(TLC), the mixture was cooled to room temperatureand poured into ice-cold water (20 mL), and theprecipitate was filtered off, washed with cold ethanol(5-7 mL), and dried.
  • 32
  • [ 61832-41-5 ]
  • [ 104-87-0 ]
  • [ 90908-89-7 ]
  • 6-(methylamino)-4-(4-methylphenyl)-5-nitro-2-(1H-pyrrol-2-yl)-4H-pyran-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With piperidine In ethanol at 90℃; for 0.25h; Sealed tube; Microwave irradiation; 4-Aryl-6-(methylamino)-5-nitro-2-(1H-pyrrol-2-yl)-4H-pyran-3-carbonitriles 4a-4o (general procedure).a. Microwave-assisted synthesis. General procedure: A 30-mL microwaveglass vial was charged with 0.2 g (1.0 mmol)of 3-oxo-3-(1H-pyrrol-2-yl)propanenitrile (1), 1.0 mmol of aromatic aldehyde 3a-3o, 0.12 g(1.0 mmol) of (E)-N-methyl-1-(methylsulfanyl)-2-nitroethenamine (2), and a catalytic amount of piperidinein 10 mL of ethanol. The vial was sealed, placedin a microwave chamber, and irradiated at 90°C withstirring for 15-20 min. After completion of the reaction(TLC), the mixture was cooled to room temperatureand poured into ice-cold water (20 mL), and theprecipitate was filtered off, washed with cold ethanol(5-7 mL), and dried.
  • 33
  • [ 61832-41-5 ]
  • [ 123-11-5 ]
  • [ 90908-89-7 ]
  • 4-(4-methoxyphenyl)-6-(methylamino)-5-nitro-2-(1H-pyrrol-2-yl)-4H-pyran-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With piperidine In ethanol at 90℃; for 0.25h; Sealed tube; Microwave irradiation; 4-Aryl-6-(methylamino)-5-nitro-2-(1H-pyrrol-2-yl)-4H-pyran-3-carbonitriles 4a-4o (general procedure).a. Microwave-assisted synthesis. General procedure: A 30-mL microwaveglass vial was charged with 0.2 g (1.0 mmol)of 3-oxo-3-(1H-pyrrol-2-yl)propanenitrile (1), 1.0 mmol of aromatic aldehyde 3a-3o, 0.12 g(1.0 mmol) of (E)-N-methyl-1-(methylsulfanyl)-2-nitroethenamine (2), and a catalytic amount of piperidinein 10 mL of ethanol. The vial was sealed, placedin a microwave chamber, and irradiated at 90°C withstirring for 15-20 min. After completion of the reaction(TLC), the mixture was cooled to room temperatureand poured into ice-cold water (20 mL), and theprecipitate was filtered off, washed with cold ethanol(5-7 mL), and dried.
  • 34
  • [ 61832-41-5 ]
  • [ 86-81-7 ]
  • [ 90908-89-7 ]
  • 6-(methylamino)-5-nitro-2-(1H-pyrrol-2-yl)-4-(3,4,5-trimethoxyphenyl)-4H-pyran-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With piperidine In ethanol at 90℃; for 0.25h; Sealed tube; Microwave irradiation; 4-Aryl-6-(methylamino)-5-nitro-2-(1H-pyrrol-2-yl)-4H-pyran-3-carbonitriles 4a-4o (general procedure).a. Microwave-assisted synthesis. General procedure: A 30-mL microwaveglass vial was charged with 0.2 g (1.0 mmol)of 3-oxo-3-(1H-pyrrol-2-yl)propanenitrile (1), 1.0 mmol of aromatic aldehyde 3a-3o, 0.12 g(1.0 mmol) of (E)-N-methyl-1-(methylsulfanyl)-2-nitroethenamine (2), and a catalytic amount of piperidinein 10 mL of ethanol. The vial was sealed, placedin a microwave chamber, and irradiated at 90°C withstirring for 15-20 min. After completion of the reaction(TLC), the mixture was cooled to room temperatureand poured into ice-cold water (20 mL), and theprecipitate was filtered off, washed with cold ethanol(5-7 mL), and dried.
  • 35
  • [ 61832-41-5 ]
  • [ 105-07-7 ]
  • [ 90908-89-7 ]
  • 4-(4-cyanophenyl)-6-(methylamino)-5-nitro-2-(1H-pyrrol-2-yl)-4H-pyran-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With piperidine In ethanol at 90℃; for 0.25h; Sealed tube; Microwave irradiation; 4-Aryl-6-(methylamino)-5-nitro-2-(1H-pyrrol-2-yl)-4H-pyran-3-carbonitriles 4a-4o (general procedure).a. Microwave-assisted synthesis. General procedure: A 30-mL microwaveglass vial was charged with 0.2 g (1.0 mmol)of 3-oxo-3-(1H-pyrrol-2-yl)propanenitrile (1), 1.0 mmol of aromatic aldehyde 3a-3o, 0.12 g(1.0 mmol) of (E)-N-methyl-1-(methylsulfanyl)-2-nitroethenamine (2), and a catalytic amount of piperidinein 10 mL of ethanol. The vial was sealed, placedin a microwave chamber, and irradiated at 90°C withstirring for 15-20 min. After completion of the reaction(TLC), the mixture was cooled to room temperatureand poured into ice-cold water (20 mL), and theprecipitate was filtered off, washed with cold ethanol(5-7 mL), and dried.
  • 36
  • [ 61832-41-5 ]
  • [ 456-48-4 ]
  • [ 90908-89-7 ]
  • 4-(3-fluorophenyl)-6-(methylamino)-5-nitro-2-(1H-pyrrol-2-yl)-4H-pyran-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With piperidine In ethanol at 90℃; for 0.25h; Sealed tube; Microwave irradiation; 4-Aryl-6-(methylamino)-5-nitro-2-(1H-pyrrol-2-yl)-4H-pyran-3-carbonitriles 4a-4o (general procedure).a. Microwave-assisted synthesis. General procedure: A 30-mL microwaveglass vial was charged with 0.2 g (1.0 mmol)of 3-oxo-3-(1H-pyrrol-2-yl)propanenitrile (1), 1.0 mmol of aromatic aldehyde 3a-3o, 0.12 g(1.0 mmol) of (E)-N-methyl-1-(methylsulfanyl)-2-nitroethenamine (2), and a catalytic amount of piperidinein 10 mL of ethanol. The vial was sealed, placedin a microwave chamber, and irradiated at 90°C withstirring for 15-20 min. After completion of the reaction(TLC), the mixture was cooled to room temperatureand poured into ice-cold water (20 mL), and theprecipitate was filtered off, washed with cold ethanol(5-7 mL), and dried.
  • 37
  • [ 61832-41-5 ]
  • [ 874-42-0 ]
  • [ 90908-89-7 ]
  • 4-(2,4-dichlorophenyl)-6-(methylamino)-5-nitro-2-(1H-pyrrol-2-yl)-4H-pyran-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With piperidine In ethanol at 90℃; for 0.333333h; Sealed tube; Microwave irradiation; 4-Aryl-6-(methylamino)-5-nitro-2-(1H-pyrrol-2-yl)-4H-pyran-3-carbonitriles 4a-4o (general procedure).a. Microwave-assisted synthesis. General procedure: A 30-mL microwaveglass vial was charged with 0.2 g (1.0 mmol)of 3-oxo-3-(1H-pyrrol-2-yl)propanenitrile (1), 1.0 mmol of aromatic aldehyde 3a-3o, 0.12 g(1.0 mmol) of (E)-N-methyl-1-(methylsulfanyl)-2-nitroethenamine (2), and a catalytic amount of piperidinein 10 mL of ethanol. The vial was sealed, placedin a microwave chamber, and irradiated at 90°C withstirring for 15-20 min. After completion of the reaction(TLC), the mixture was cooled to room temperatureand poured into ice-cold water (20 mL), and theprecipitate was filtered off, washed with cold ethanol(5-7 mL), and dried.
  • 38
  • [ 61424-76-8 ]
  • [ 61832-41-5 ]
  • C13H8N2O4S [ No CAS ]
  • 2-(methylamino)-3-nitro-5H-chromeno[2,3-b]pyridin-5-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 75% 2: 16% With trifluorormethanesulfonic acid In ethanol for 0.5h; Reflux; General Procedure for the Synthesis of 3. General procedure: To a round-bottomed flash containting substritued 2-amino-3-formylchromones (0.5 mmol) andEtOH (5 mL) was added the corresponding substituted 1-(methylthio)-2-nitroenamine derivatives (0.6mmol).Then CF3SO3H was added dropwise to the mixture. The reaction solution was stirred at roomtemperature for 0.5-5h. After completion of the reaction (TLC), the reaction mixture was quenchedwith H2O (20 mL) and extracted with DCM (3×10 mL). The combined organic layer was washed withbrine (2×10 mL), dried over MgSO4, and concentrated under reduced pressure. The crude residue wasthen purified by column chromatography on silica gel using n-heptane /DCM mixture as eluent toafford the pure target compounds 3.
  • 39
  • [ 61424-76-8 ]
  • [ 61832-41-5 ]
  • 2-(methylamino)-3-nitro-5H-chromeno[2,3-b]pyridin-5-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With trifluorormethanesulfonic acid In ethanol for 0.5h; Reflux; General Procedure for the Synthesis of 3. General procedure: To a round-bottomed flash containting substritued 2-amino-3-formylchromones (0.5 mmol) andEtOH (5 mL) was added the corresponding substituted 1-(methylthio)-2-nitroenamine derivatives (0.6mmol).Then CF3SO3H was added dropwise to the mixture. The reaction solution was stirred at roomtemperature for 0.5-5h. After completion of the reaction (TLC), the reaction mixture was quenchedwith H2O (20 mL) and extracted with DCM (3×10 mL). The combined organic layer was washed withbrine (2×10 mL), dried over MgSO4, and concentrated under reduced pressure. The crude residue wasthen purified by column chromatography on silica gel using n-heptane /DCM mixture as eluent toafford the pure target compounds 3.
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