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[ CAS No. 13654-62-1 ] {[proInfo.proName]}

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Chemical Structure| 13654-62-1
Chemical Structure| 13654-62-1
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Product Details of [ 13654-62-1 ]

CAS No. :13654-62-1 MDL No. :MFCD11934304
Formula : C4H7NO2S Boiling Point : -
Linear Structure Formula :- InChI Key :UMCQAGDGGSOQGK-UHFFFAOYSA-N
M.W : 133.17 Pubchem ID :18790956
Synonyms :

Calculated chemistry of [ 13654-62-1 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.75
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 30.05
TPSA : 66.31 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.28 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.6
Log Po/w (XLOGP3) : -0.24
Log Po/w (WLOGP) : 1.03
Log Po/w (MLOGP) : -0.6
Log Po/w (SILICOS-IT) : -0.14
Consensus Log Po/w : 0.13

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.38
Solubility : 55.2 mg/ml ; 0.415 mol/l
Class : Very soluble
Log S (Ali) : -0.69
Solubility : 26.9 mg/ml ; 0.202 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.05
Solubility : 11.8 mg/ml ; 0.0883 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.6

Safety of [ 13654-62-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501 UN#:N/A
Hazard Statements:H302-H312-H332 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 13654-62-1 ]

* 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 [ 13654-62-1 ]

[ 13654-62-1 ] Synthesis Path-Downstream   1~20

  • 1
  • [ 53250-09-2 ]
  • [ 13654-62-1 ]
YieldReaction ConditionsOperation in experiment
98% With methyltri-n-octylammonium dihydrogenophosphate; sodium tungstate (VI) dihydrate; dihydrogen peroxide at 20 - 50℃; for 4h;
  • 3
  • [ 107-14-2 ]
  • [ 594-44-5 ]
  • [ 13654-62-1 ]
YieldReaction ConditionsOperation in experiment
Stage #1: Ethanesulfonyl chloride With sodium hydrogencarbonate; sodium sulfite In water at 100℃; for 0.5h; Microwave irradiation; Stage #2: chloroacetonitrile In water at 100℃; for 0.333333h; Microwave irradiation;
  • 4
  • [ 20035-08-9 ]
  • [ 107-14-2 ]
  • [ 13654-62-1 ]
YieldReaction ConditionsOperation in experiment
1.3 g In acetonitrile; at 100℃; for 5h;Inert atmosphere; At room temperature, nitrogen gas atmosphere, 1.2 g of chloroacetonitrile, acetonitrile 5.0 mL and <strong>[20035-08-9]sodium ethanesulfinate</strong> 1.98g were added and heated to 100C. for 5 hours followed by stirring. After cooling to room temperature, it was concentrated under reduced pressure and diluted with ethyl acetate. Water was added, the mixture was washed and separated, and the obtained organic layer was concentrated to obtain 1.3 g of (ethylsulfonyl)acetonitrile.
  • 5
  • [ 102-52-3 ]
  • [ 13654-62-1 ]
  • 2-bromo-3-ethanesulfonylpyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
90 mg Stage #1: malonaldehydebis(dimethylacetal) With acetic anhydride; zinc(II) chloride at 100℃; for 0.5h; Inert atmosphere; Stage #2: 2-(ethanesulfonyl)acetonitrile In toluene for 3h; Stage #3: With hydrogen bromide; acetic acid at 30℃; for 1h; 1 1.2 g of acetic anhydride, 16.3 mg of zinc chloride and 980 mg of 1,1,3,3-tetramethoxypropane were added to a three-neck eggplant-shaped flask at room temperature under a nitrogen atmosphere. The resulting mixture was stirred at 100°C. for 30 minutes. To the resulting mixture, 531.0 mg of (ethylsulfonyl) acetonitrile and 1.0 g of toluene were added. The resulting mixture was stirred for 3 hours, cooled to room temperature and concentrated in vacuo. 3.2 g of hydrogen bromide in 20% acetic acid solution was added to the obtained mixture, and the mixture was stirred at 30°C. for 1 hour. To the resulting mixture was added a mixture of water and hexane-diethyl ether (1:1). The obtained mixture was adjusted to pH=7 with saturated sodium bicarbonate water and separated. The obtained organic layer was washed with saturated brine and concentrated under reduced pressure to obtain 90 mg of 2-bromo-3-ethanesulfonylpyridine.
  • 6
  • [ 13654-62-1 ]
  • [ 13070-22-9 ]
  • 2-ethylsulfonyl-5-(N,N-diethylamino)-2,4-pentadienenitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
95.5% With 2,2'-iminobis[ethanol] at 80℃; for 0.5h; Microwave irradiation; Green chemistry; 2 Example 2: Preparation of 2-ethylsulfonyl-5-(N,N-diethylamino)-2,4-pentadienenitrile In a 500 mL three-necked flask equipped with a thermometer, 66.6 g (0.5 mol) of ethyl cyanoethylsulfone , 20 mL of diethanolamine and 124 mL (1.0 mol) of 3-diethylaminoprop-2-enal were added, mixed well, the prepared reactor into the microwave instrument, set the microwave radiation conditions, the temperature of 80 °C, microwave power of 200W and the frequency of 915MHz under the conditions of the reaction, TLC detection (petroleum ether: methylene chloride 1: 2 expansion, sublimation iodine color) ethyl cyanomethylsulfone reaction is complete, the reaction time 0.5h. Add the mass fraction of 10% potassium hydroxide solution to adjust the pH = 7-8, liquid, the aqueous layer was extracted with 100 mL of methyl acetate and extracted three times. The organic layer was combined and the organic phase was recovered by distillation of propyl acetate under reduced pressure to give 115.7 g of a pale yellow solid, mp 155-157 °C and a yield of 95.5%.
95.9% With sodium ethanolate at 100℃; Sonication; 2 Example 2 Preparation of 2-ethylsulfonyl-5- (N, N-diethyl) amino-2,4-pentadienitrile In a 500 mL three-necked round bottom flask,124 mL (1.0 mol) of 3-diethylaminoacrolein was added,10 mL of sodium ethoxide and 66.6 g (0.5 mol) of ethyl cyanoethyl ethyl sulfone,Mix well, the prepared reactor into the ultrasonic instrument,Set the ultrasonic radiation conditions, at a temperature of 100 ,Ultrasonic power of 300W and the frequency of 80KHz reaction conditions, TLC test Measured (petroleum ether: dichloromethane 1: 3 start, sublimation of iodine color) ethyl cyanoethyl ethyl sulfone reaction was complete, add deionized water 10mL impurity The product was distilled off with organic phase to give 116.2 g of light yellow solid with a melting point of 155-157 ° C and a yield of 95.9%.
93.5% With N-ethyl-N-ethylpiperidinium chloride at 65℃; for 10h; 2 Example 2: Preparation of 2-ethylsulfonyl-5- (N, N-diethyl) amino-2,4-pentadienitrile The reactor was charged with 66.6 g (0.5 mol) of ethyl cyanoethyl ethyl sulfone, 50 mL of N-ethyl-N-ethylpiperidine chloride, Ethylacrolein 124mL (1.0mol), mixed well, the water bath heated to 65 temperature and incubated for 10h reaction, TLC Measure (petroleum ether: dichloromethane 1: 3 expand, sublimation of iodine color) ethyl cyanoethyl sulfone reaction completely, cooled to room temperature, the organic solvent Toluene extraction 60mL × 3, the remaining phase ionic liquid washing, vacuum drying repeatedly used, the organic phase is distilled off under reduced pressure solvent toluene recovery, 113.3 g of a pale yellow solid was obtained, melting at 155-157 ° C. The yield was 93.5%
In ethyl acetate at 50℃; 4 Example 4 Preparation of 2-fluoro-3-ethylsulfonylpyridine In a 500 mL three-necked flask equipped with a thermometer, 61 mL (0.5 mol) of 3-diethylaminoacrolein and 200 mL of ethyl acetate were added, followed by addition of 66.6 g (0.5 mol) of ethyl cyanoethyl sulfone, Reaction at 50 ° C, TLC detection (petroleum ether: methylene chloride 1: 2 expansion, sublimed iodine color) 3-diethylamino acrolein reaction is complete, then cooled to 5 ° C, the temperature is 5 ° C The HF gas was followed by HPLC until the reaction was completed.After the completion of the reaction, the aqueous solution was adjusted to pH 7-8, and the aqueous layer was extracted with 100 mL of ethyl acetate. The organic layers were combined, dried over a molecular sieve overnight, filtered and the solvent was removed under reduced pressure to give compound 4 (Structural formula see Table 1), namely 2-fluoro-3-ethylsulfonylpyridine, light brown liquid 80.4g, the yield of 85.0%.
With tetraethylammonium chloride In water at 50℃; for 3h; 2 Preparation of 2-ethylsulfonyl-5- (N, N-diethyl) amino-2,4-pentadienenitrile In a 500 mL three-necked round bottom flask, 124 mL (1.0 mol) of 3-dimethylaminopropene was added,(0.5 mol) of ethyl cyanoethylsulfone, 5.0 g of tetraethylammonium chloride and 200 mL of deionized water were mixed uniformly,Heated to 50 , constant temperature reaction for about 3h, to 3-dimethylaminopropenal reaction completely (HPLC detection),Vacuum distillation in addition to 60mL water, cooled to room temperature, crystallization, filtration crude product,And then recrystallized from anhydrous ethanol to give pale yellow solid 116.6g, melting point of 155-157 ,The yield was 96.2%. The product was characterized by HR-MS, i.e. 2-ethylsulfonyl-5- (N, N-diethyl) amino-2,4-pentadienenitrile.

  • 7
  • [ 25186-34-9 ]
  • [ 13654-62-1 ]
  • C7H10N2O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With diethylamine at 100℃; Microwave irradiation; Green chemistry; 9 In 500mL three-necked flask reactor equipped with a thermometer, ethyl cyanoethylsulfone was added 66.6g (0.5mol), diethylamine 20mL, 3-aminoprop-2-enal 60mL (0.5mol), mixed evenly, the prepared reactor into the microwave instrument, set the microwave radiation conditions, 100 ° C, microwave power of 2000 W and frequency of 2450MHz under the conditions of reaction, TLC detection (petroleum ether: methylene chloride 1: 2 expansion, sublimed iodine color) 3-aminoprop-2-enal was completely reacted to prepare an intermediate. Cooled to room temperature, into the HI gas, at room temperature reaction, HPLC tracking reaction until the end of the reaction time 15min. Add 5% potassium hydroxide solution to adjust the pH = 7-8, the liquid layer, ethyl acetate 100mL × 3 times extraction, combined organic layer, washed with water, molecular sieve drying, filtration, evaporation solvent ethyl acetate recovery ,2-iodo-3-ethylsulfonylpyridine, 137.4 g of pale brown crystals, a melting point of 72-74 ° C and a yield of 92.5%.
In ethyl acetate Reflux; 3 Example 3 Synthesis of 2-iodo-3-ethylsulfonylpyridine In a 500 mL three-necked flask equipped with a thermometer, 60 mL (0.5 mol) of 3-aminopalonal and 200 mL of ethyl acetate were added, followed by addition of 66.6 g (0.5 mol) of ethyl cyanoethylsulfone, homogeneously mixed, heated to reflux, TLC detection (petroleum ether: methylene chloride 1: 2 expansion, sublimed iodine color) 3-aminophenaldehyde reaction is complete, then cooled to 25 ° C, and then into the HI gas, HPLC tracking reaction until the end of the reaction. After the reaction was completed, the reaction was carried out by adding 10% potassium hydroxide solution to adjust the pH = 7-8. The aqueous layer was extracted with ethyl acetate 50 mL x 3 times. The organic phase was combined and the organic phase was depressurized to remove the solvent. Compound 3 (structural formula is shown in Table 1), namely 2-iodo-3-ethylsulfonylpyridine, light brown crystals, 135.2 g, melting point 72-74 ° C, yield 91.0%.
With triethylamine at 10℃; Sonication; 9 Example 9 Synthesis of 2-iodo-3-ethylsulfonylpyridine In a 500 mL three-necked flask equipped with a thermometer,First, 60 mL (0.5 mol) of 3-aminoacrolein and triethylamine were added10mL,Then add ethyl cyanoethyl sulfone 66.6g (0.5mol), mix well,The prepared reactor into the ultrasonic instrument, set the ultrasonic radiation conditions,At a temperature of 10 ° C,Ultrasound power of 50W and frequency of 22KHz reaction conditions, TLCDetection (petroleum ether: dichloromethane 1: 2 expansion, sublimation of iodine color) 3-aminoacrolein reaction was complete, cooled to 25 ° C, into the HIGas, ultrasonic irradiation conditions as above, the reaction temperature is 25 , HPLC tracking reaction until the end of the reaction. Then the reaction is completed After adding 10% mass fraction of potassium hydroxide solution to adjust the pH = 7-8, liquid separation, the aqueous layer was extracted with dichloromethane 100mL × 3 times The organic layers were combined and washed with 10 mL of deionized water. The organic layer was washed with water and separated. The organic layer was dried over molecular sieves overnight The organic phase was removed by filtration under reduced pressure to give 2-iodo-3-ethylsulfonylpyridine, 135.5 g of pale brown crystals, m.p. 72-74 ° C, yield 91.2%.
  • 8
  • [ 13654-62-1 ]
  • [ 927-63-9 ]
  • C9H14N2O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With L-Tryptophan; at 50℃;Microwave irradiation; Green chemistry; A 500 mL three-necked flask reactor equipped with a thermometer was charged with 66.6 g (0.5 mol) of ethyl cyanoethylsulfone , 50 mL of L-tryptophan, 62 mL (0.5 mol) of 3-dimethylaminoprop-2-enal, mixed well, the prepared reactor into the microwave, set the microwave radiation conditions, 50 C temperature, microwave power of 500W and the frequency of 915MHz under the conditions of the reaction, TLC detection (petroleum ether: dichloromethane 1: 2 expansion, sublimation iodine color) 3-dimethylaminoprop-2-enal was completely reacted to prepare an intermediate. Cooled to 5 C, passed HF gas, reacted at 5 C, and the reaction was followed by HPLC until the reaction was completed and the reaction time was 50 min. Add 5% potassium hydroxide solution to adjust the pH = 7-8, separated, the water layer with ethyl acetate 100mL × 3 times extraction, the organic layer, washed with water, separated, dried over anhydrous sodium sulfate, filtered and evaporated. After solvent ethyl acetate was recovered. The yield of 2-fluoro-3-ethylsulfonylpyridine and 86.6 g of a light brown liquid was 91.5%.
In dichloromethane;Reflux; In a 500 mL three-necked flask equipped with a thermometer, 62 mL (0.5 mol) of 3-dimethylaminopropene and 100 mL of dichloromethane were added, followed by addition of 66.6 g (0.5 mol) of ethyl cyanoethyl sulfone, homogeneously mixed, Reaction, TLC detection (petroleum ether: methylene chloride 1: 2 expansion, sublimed iodine color) 3-dimethylaminopropenal reaction completely, then cooled to 25 C, into the HBr gas, HPLC tracking reaction until the end of the reaction. After the completion of the reaction, the addition of 30% sodium hydroxide solution to adjust the pH = 7-8, separated, the water layer with dichloromethane 120mL × 3 times extraction, the organic layer, 10mL of deionized water washed and separated, The organic layer was dried over Na2SO4, filtered and the solvent was removed under reduced pressure to give compound 2 (structural formula see Table 1), namely 2-bromo-3-ethylsulfonylpyridine, 112.5g as pale yellow crystals, 65-67 C, the yield was 90.0%.
With benzyltriethylammonium bromide; In water; at 40℃; In a 500 mL three-necked flask equipped with a thermometer, 62 mL (0.5 mol) of 3-dimethylaminopropenal was added,1.0 g of triethylbenzylammonium bromide and 100 mL of deionized water were added to 66.6 g (0.5 mol) of ethyl cyanoethyl sulfone, and the mixture was homogeneously reacted at a temperature of 40 C,TLC detection (petroleum ether: methylene chloride 1: 2 expansion, sublimed iodine color) 3-dimethylaminopropenal reaction is complete,Cooled to 25 C, HBr gas was passed at 25 C, and the reaction was followed by HPLC until the reaction was completed.Then after the end of the reaction, add the mass fraction of 30% sodium hydroxide solution to adjust the pH = 7-8, separated, the water layer with dichloromethane 60mL × 3 times extraction,The organic layer was combined with 10 mL of deionized water and then partitioned. The organic layer was dried over Na2SO4, filtered and the solvent was removed under reduced pressure to give 2-bromo-3-ethylsulfonylpyridine,Pale yellow crystals 116.3g, melting point of 65-67 C, the yield was 93.0%
  • 9
  • [ 13654-62-1 ]
  • [ 927-63-9 ]
  • 2-bromo-3-ethanesulfonylpyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
93.9% A reactor was charged with 66.6 g (0.5 mol) of ethyl cyanoethyl ethyl sulfone, 50 mL of 1-dodecyl-3-methylimidazolium chloride,50mL (0.4mol) <strong>[927-63-9]3-dimethylaminoacrolein</strong> was added and mixed well. The mixture was heated in an oil bath at 90 for 3h, and the reaction was monitored by TLC. The crude product was chromatographed by TLC (petroleum ether: dichloromethane 1: 2, Dimethylaminoacrolein reaction is complete, cooled to room temperature,60 mL of organic solvent 1,2-dichloroethane was extracted three times,Yu phase ionic liquid water washing, vacuum drying repeated use, The organic phase leads to dry HBr gas,The reaction was followed by HPLC until the reaction was complete.Join mass fraction of 20% sodium carbonate solution to adjust the pH = 7-8, points The liquid and the aqueous layer were extracted with 100 mL × 3 of 1,2-dichloroethane. The organic layers were combined, washed with water, separated from water, dried over molecular sieves, filtered and reduced in pressure The solvent 1,2-dichloroethane was distilled off to obtain 2-bromo-3-ethylsulfonylpyridine, 117.4 g of light yellow crystals, melting at 65 -67 C, 93.9% yield,
  • 10
  • [ 13654-62-1 ]
  • [ 927-63-9 ]
  • 2-fluoro-3-ethylsulfonylpyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
90.7% A reactor was charged with 66.6 g (0.5 mol) of ethyl cyanoethyl ethyl sulfone, 50 mL of 1-butyl-3-methylimidazolium trifluoroacetate,(0.5mol) of <strong>[927-63-9]3-dimethylaminoacrolein</strong> was added and mixed uniformly. The electric furnace was heated to 120 C and incubated for 0.5h for reaction. TLC (petroleum ether: dichloromethane 1: 2 expansion and sublimation of iodine) 3 - dimethylaminoacrolein reaction was complete, cooled to 5 C, the organic solvent was extracted with toluene 60mL 3 times, the remaining ionic liquid was washed with water, dried in vacuo and reused, the organic phase was passed into a dryHF gas, followed by HPLC until the reaction is complete. Join mass fraction of 20% potassium carbonate solution to adjust pH = 7-8, liquid separation, The aqueous layer was extracted with toluene 100 mL × 3, and the organic layers were combined, washed with water, separated by liquid, dried over molecular sieves, and filtered. The solvent toluene was distilled off under reduced pressure This was recovered to give 85.8 g of 2-fluoro-3-ethylsulfonylpyridine as a pale brown liquid in a yield of 90.7%.
  • 11
  • [ 25186-34-9 ]
  • [ 13654-62-1 ]
  • [ 1299474-20-6 ]
YieldReaction ConditionsOperation in experiment
93.9% Stage #1: 3-aminoprop-2-enal; 2-(ethanesulfonyl)acetonitrile With 1-hydroxyethyl-3-methyl-1H-imidazolium chloride at 110℃; for 2h; Stage #2: With hydrogen iodide 9 Example 9: Preparation of 2-iodo-3-ethylsulfonylpyridine The reactor was charged with 66.6g (0.5mol) of ethyl cyanoethyl ethyl sulfone, 50mL of 1-hydroxyethyl-3-methylimidazolium chloride,3-amino acrolein 60mL (0.5mol), mixed well, heated to 110 temperature and incubated for 2h reaction, TLC detection(Petroleum ether: dichloromethane 1: 2 expansion, sublimation of iodine color) 3 - amino acrolein reaction was complete, cooled to room temperature, the organic solvent B Acid ethyl ester 60mL extracted three times, the remaining ionic liquid water washing, vacuum drying repeated use, the organic phase was introduced dry HI gas,The reaction was followed by HPLC until the reaction was complete. Add 10% mass fraction of ammonia to adjust the pH = 7-8, liquid separation, the aqueous layer with acetic acid Ester 100mL × 3 extraction, the combined organic layer, washed with water, liquid separation, molecular sieve drying, filtration, the solvent was distilled off under reduced pressure ethyl acetate 2-iodo-3-ethylsulfonylpyridine, 139.5 g of light brown crystals, melting at 72-74 ° C, yield 93.9%.
  • 12
  • [ 13654-62-1 ]
  • C15H19F2NO3 [ No CAS ]
  • C19H26F2N2O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% Stage #1: 2-(ethanesulfonyl)acetonitrile; C15H19F2NO3 With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; Stage #2: With sodium tetrahydroborate; isopropyl alcohol at 10 - 20℃; for 0.833333h; PREPARATION OF INTERMEDIATE B23’’ Intermediate B6’’ (84 g, 281 mmol) obtained via method B’’ as a DCM solution (677 mL) and 2-(ethanesulfonyl)acetonitrile (50 g, 339 mmol) was added at 20 °C in an EasyMax(Registered trademark) Advanced Synthesis Workstation (Mettler-Toledo), then DBU (0.84 mL, 5.61 mmol) was added. The reaction mixture was stirred overnight at 20 °C. Then acetic acid (1.61 mL, 28 mmol) was added at 20 °C, and the reaction mixture was stirred for 90 min. The reaction mixture was then concentrated. THF (677 mL) was added, and the reaction mixture was concentrated to 600 mL after which 2-propanol (85 mL) was added. This solution was cooled to 0°C. Sodium borohydride (6.37, 168 mmol) was added in portions to the reaction mixture over 20 min at 10 °C and then it was stirred for another 30 min at rt. Subsequently HCl (1 M in water, 196 mL) was added at 0 °C, then the layers were separated and the organic layer was washed with a solution of 90 g NaCl in 540 mL water. The organic layer was separated, dried (MgSO 4), filtered and evaporated. The residue was purified by chromatography using a 4 liter glass fritted filter filled with silica gel, using heptane/ EtOAc going from 100:0 to 60:40 as eluent. The product fractions were collected and evaporated providing intermediate B23’’ (102 g, 87%).
  • 13
  • [ 13654-62-1 ]
  • C15H20FNO3 [ No CAS ]
  • C19H27FN2O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With methanol; sodium tetrahydroborate; magnesium oxide In 2-methyltetrahydrofuran
  • 14
  • [ 25090-33-9 ]
  • [ 13654-62-1 ]
  • 3-(3,4-dihydro-2H-pyran-5-yl)-2-(ethylsulfonyl)acrylonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With ammonium acetate; acetic acid at 100℃; for 6h; 15 Production of 3- (3,4-dihydro-2H-pyran-5-yl) -2- (ethylsulfonyl) acrylonitrile 1.12 g (0.01 mol) of 3,4-dihydro-2H-pyran-5-carbaldehyde and 1.33 g (0.01 mol) of 2- (ethylsulfonyl) acetonitrile were dissolved in 2 mL of acetic acid.Add 0.15 g (2 mmol) of ammonium acetate andThe mixture was heated to 100 ° C. for 6 hours with stirring. After allowing to coolAdd water to the reaction mixture, extract with ethyl acetate, water the organic layer,It was washed with saturated aqueous sodium hydrogen carbonate and then saturated brine, and dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (ethyl acetate-hexane 1: 2) to obtain 1.50 g (66%) of the title compound.
  • 15
  • [ 20074-80-0 ]
  • [ 13654-62-1 ]
  • 7-chloro-2-(ethylsulfonyl)hepta-2-enenitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With piperidine; acetic acid at 50℃; for 1h; 1 Production of 7-Chloro-2- (ethylsulfonyl) hepta-2-enenitrile 5-Chloropentanal 1.21 g (0.01 mol) and2- (Ethylsulfonyl) acetonitrile1.33 g (0.01 mol) was dissolved in 4 mL of acetic acid and heated to an internal temperature of 50 ° C. Under stirring, a solution of 0.17 g (2 mmol) of piperidine in 1 mL of acetic acid was added dropwise.Then, it heated to 50 degreeC for 1 hour. After allowing to cool, water was added to the reaction mixture, extracted with toluene, the organic layer was washed with water and then saturated brine, and dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was subjected to silica gel column chromatography (ethyl acetate-hexane).Purification by 1: 2) gave 1.92 g (81%) of the title compound as a viscous oil.
  • 16
  • [ 13654-62-1 ]
  • C13H9N3O4S [ No CAS ]
  • C17H13N3O6S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With ammonium acetate In acetic acid at 150℃; for 0.666667h; Sealed tube; c (Q-tube) General procedure: Arylhydrazonal 6a-6e (10 mmol)was added to active methylene compound 10a-10c(10 mmol), and the mixture was dissolved in a solutionof ammonium acetate (2 g) in acetic acid (10 mL) orin a solution of piperidine (3 drops) in absolute ethanol(10 mL). The resulting solution was loaded into a35-mL Q-tube. A Tefl on septum was placed on thetop of the tube, and an appropriate cap was used. Thereaction mixture was heated in an oil bath at 150°C for15-20 min and then cooled and poured into ice water.The solid that formed was collected by fi ltration andcrystallized from EtOH.
  • 17
  • [ 13654-62-1 ]
  • C14H12N2O3S [ No CAS ]
  • C18H16N2O5S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With ammonium acetate In acetic acid at 150℃; for 0.666667h; Sealed tube; c (Q-tube) General procedure: Arylhydrazonal 6a-6e (10 mmol)was added to active methylene compound 10a-10c(10 mmol), and the mixture was dissolved in a solutionof ammonium acetate (2 g) in acetic acid (10 mL) orin a solution of piperidine (3 drops) in absolute ethanol(10 mL). The resulting solution was loaded into a35-mL Q-tube. A Tefl on septum was placed on thetop of the tube, and an appropriate cap was used. Thereaction mixture was heated in an oil bath at 150°C for15-20 min and then cooled and poured into ice water.The solid that formed was collected by fi ltration andcrystallized from EtOH.
  • 18
  • [ 13654-62-1 ]
  • C13H9N3O5 [ No CAS ]
  • C17H13N3O7S [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With piperidine In ethanol at 150℃; for 0.333333h; Sealed tube; c (Q-tube) General procedure: Arylhydrazonal 6a-6e (10 mmol)was added to active methylene compound 10a-10c(10 mmol), and the mixture was dissolved in a solutionof ammonium acetate (2 g) in acetic acid (10 mL) orin a solution of piperidine (3 drops) in absolute ethanol(10 mL). The resulting solution was loaded into a35-mL Q-tube. A Tefl on septum was placed on thetop of the tube, and an appropriate cap was used. Thereaction mixture was heated in an oil bath at 150°C for15-20 min and then cooled and poured into ice water.The solid that formed was collected by fi ltration andcrystallized from EtOH.
  • 19
  • [ 13654-62-1 ]
  • C14H12N2O4 [ No CAS ]
  • C18H16N2O6S [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With ammonium acetate In acetic acid at 150℃; for 0.666667h; Sealed tube; c (Q-tube) General procedure: Arylhydrazonal 6a-6e (10 mmol)was added to active methylene compound 10a-10c(10 mmol), and the mixture was dissolved in a solutionof ammonium acetate (2 g) in acetic acid (10 mL) orin a solution of piperidine (3 drops) in absolute ethanol(10 mL). The resulting solution was loaded into a35-mL Q-tube. A Tefl on septum was placed on thetop of the tube, and an appropriate cap was used. Thereaction mixture was heated in an oil bath at 150°C for15-20 min and then cooled and poured into ice water.The solid that formed was collected by fi ltration andcrystallized from EtOH.
  • 20
  • [ 13654-62-1 ]
  • C15H19F2NO3 [ No CAS ]
  • C19H24F2N2O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-(ethanesulfonyl)acetonitrile; C15H19F2NO3 With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 19h; Inert atmosphere; Stage #2: With acetic acid In dichloromethane at 20℃; for 1.5h; Inert atmosphere;
Same Skeleton Products
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