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[ CAS No. 6314-42-7 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 6314-42-7
Chemical Structure| 6314-42-7
Chemical Structure| 6314-42-7
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Product Details of [ 6314-42-7 ]

CAS No. :6314-42-7 MDL No. :MFCD00052505
Formula : C9H7NOS Boiling Point : -
Linear Structure Formula :- InChI Key :GYSCBCSGKXNZRH-UHFFFAOYSA-N
M.W : 177.22 Pubchem ID :237073
Synonyms :

Calculated chemistry of [ 6314-42-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 49.92
TPSA : 71.33 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.85 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.67
Log Po/w (XLOGP3) : 2.15
Log Po/w (WLOGP) : 2.0
Log Po/w (MLOGP) : 1.55
Log Po/w (SILICOS-IT) : 2.76
Consensus Log Po/w : 2.03

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.78
Solubility : 0.293 mg/ml ; 0.00165 mol/l
Class : Soluble
Log S (Ali) : -3.28
Solubility : 0.093 mg/ml ; 0.000525 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.93
Solubility : 0.209 mg/ml ; 0.00118 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.75

Safety of [ 6314-42-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 6314-42-7 ]

* 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 [ 6314-42-7 ]

[ 6314-42-7 ] Synthesis Path-Downstream   1~36

YieldReaction ConditionsOperation in experiment
Bromid I, NH3;
1.H Benzo[b]thiophene-2-carboxamide, 6-methoxy-3-(1-methylethoxy)-N- 1H-tetrazol-5-yl EXAMPLE 1(H) Benzo[b]thiophene-2-carboxamide, 6-methoxy-3-(1-methylethoxy)-N- 1H-tetrazol-5-yl A mixture of benzo[b]thiophene-2-carboxylic acid-6-methoxy-3(1-methylethoxy) (10.41 g, 0.039 mole) and 1,1'-carbonyldiimidazole (7.61 g, 0.047 mole) in acetonitrile (200 ml) is refluxed with stirring under nitrogen for 80 minutes. A solution of 5-aminotetrazole (3.99 g, 0.047 mole) and triethylamine (4.75 g, 0.047 mole) in acetonitrile (100 ml) is added dropwise. The mixture is heated at reflux for 21.5 hours, then most of the acetonitrile is removed under water aspirator pressure at 40°. The residue is treated with cold water (~700 ml) then acidified with acetic acid (14.5 g). The resulting solid is separated by filtration, washed with water, then with ether, and dried to give 12.1 g of a solid. Recrystallization from methanol gives 11.06 g (84.9%) of analytically pure product, mp 237°-9° C. (dec).
6.H Benzo[b]thiophene-2-carboxamide, 3-(1-methylethoxy)-5-methyl-N-1H-tetrazol-5-yl EXAMPLE 6(H) Benzo[b]thiophene-2-carboxamide, 3-(1-methylethoxy)-5-methyl-N-1H-tetrazol-5-yl A mixture of benzo[b]thiophene-2-carboxylic acid-5-methyl-3(1-methylethoxy) (8.5 g, 0.034 mole), 1,1'-carbonyldiimidazole (6.62 g, 0.041 mole), 5-aminotetrazole (3.47 g, 0.041 mole), and triethylamine (4.13 g, 0.041 mole) in acetonitrile (300 ml) is treated according to the procedure in Example 1(H). There is obtained 10.32 g of the product, mp 247°-9° C. (dec). Recrystallization from methanol gives 8.17 g (80.8%) of analytically pure product, mp 247°-9° C. (dec).
7.B Benzo[b]thiophene-2-carboxamide, 6-chloro-3(1-methyl-ethoxy)-N-1H-tetrazol-5-yl EXAMPLE 7(B) Benzo[b]thiophene-2-carboxamide, 6-chloro-3(1-methyl-ethoxy)-N-1H-tetrazol-5-yl A mixture of benzo[b]thiophene-2-carboxylic acid-6-chloro-3-(1-methylethoxy) (8.05 g, 0.03 mole) 1,1'-carbonyldiimidazole (5.79 g, 0.036 mole), 5-aminotetrazole (3.04 g, 0.036 mole) and triethylamine (3.61 g, 0.036 mole) in acetonitrile (200 ml) is treated according to the procedure in Example 1(H). There is obtained 9.8 g of the product, mp 250°-1° C. (dec). Recrystallization from dimethylformamidemethanol gives 8.4 g (84%) of analytically pure product, mp 249°-251° C. (dec).
The following are non-limiting examples of other analogs prepared by the procedures described herein above. ... Naphthylene-1-carboxylic acid {1-[(2-ethoxy-5-oxo-tetrahydrofuran-3-yl-carbamoyl)methyl]-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-yl}-amide; Benzo[b]thiophene-2-carboxylic {1-[(2-hydroxy-5-oxo-tetrahydrofuran-3-yl-carbamoyl)methyl]-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-yl}-amide; Benzo[b]thiophene-2-carboxylic {1-[(2-ethoxy-5-oxo-tetrahydrofuran-3-yl-carbamoyl)methyl]-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-yl}-amide; 3-Fluoro-N-{1-[(2-hydroxy-5-oxo-tetrahydrofuran-3-ylcarbamoyl)methyl]-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-yl}-benzamide; ...
The following are non-limiting examples of other analogs prepared by the procedures described herein above. ... Naphthylene-1-carboxylic acid {1-[(2-hydroxy-5-oxo-tetrahydrofuran-3-yl-carbamoyl)methyl]-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-yl}-amide; Naphthylene-1-carboxylic acid {1-[(2-ethoxy-5-oxo-tetrahydrofuran-3-yl-carbamoyl)methyl]-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-yl}-amide; Benzo[b]thiophene-2-carboxylic {1-[(2-hydroxy-5-oxo-tetrahydrofuran-3-yl-carbamoyl)methyl]-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-yl}-amide; Benzo[b]thiophene-2-carboxylic {1-[(2-ethoxy-5-oxo-tetrahydrofuran-3-yl-carbamoyl)methyl]-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-yl}-amide; ...

  • 6
  • [ 1136-76-1 ]
  • [ 6314-42-7 ]
  • C20H16N4O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% With diphenylphosphoranyl azide; N-ethyl-N,N-diisopropylamine In benzene at 85℃; for 3h;
  • 7
  • [ 6314-28-9 ]
  • [ 6314-42-7 ]
YieldReaction ConditionsOperation in experiment
83% With magnesium(II) nitrate hexahydrate; urea In octane at 120℃; for 24h;
36% Stage #1: benzo[b]thiophene-2-carboxylic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 25℃; for 0.0833333h; Stage #2: With ammonium hydroxide In N,N-dimethyl-formamide at 25℃; for 0.5h;
Multi-step reaction with 2 steps 1: thionyl chloride / benzene / 2.5 h / Heating 2: NH3 / dioxane / 2 h / Ambient temperature
Multi-step reaction with 2 steps 1: thionyl chloride / toluene / 2 h / Reflux 2: ammonium hydroxide / water; dichloromethane / 1 h / 0 - 20 °C

  • 8
  • [ 6314-42-7 ]
  • Benzo[b]thiophene-2-carboximidic acid ethyl ester; hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: P2O5 / toluene / 1.) reflux, 2 h, 2.) RT, 16 h 2: gaseous HCl / diethyl ether / 24 h / 0 - 10 °C
  • 9
  • [ 6314-42-7 ]
  • [ 89197-30-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: P2O5 / toluene / 1.) reflux, 2 h, 2.) RT, 16 h 2: gaseous HCl / diethyl ether / 24 h / 0 - 10 °C
  • 10
  • [ 108735-42-8 ]
  • [ 6314-42-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 83 percent / benzene; hexane / 1 h 2: 98 percent / acetone / 1 h / Irradiation
  • 11
  • 3-(1-methylethoxy)(5.95 g, 0.025 mole) [ No CAS ]
  • [ 6314-42-7 ]
  • [ 106-95-6 ]
  • [ 530-62-1 ]
  • [ 55219-11-9 ]
  • [ 95-15-8 ]
YieldReaction ConditionsOperation in experiment
In hexane; EXAMPLE 14(B) Benzo[ b]thiophene, 2-carbonitrile-3-(1-methylethoxy) A mixture of benzo[b]thiophene-2-carboxamide, 3-(1-methylethoxy)(5.95 g, 0.025 mole), 1,1'-carbonyldiimidazole (8.2 g, 0.051 mole) and allyl bromide (24.5 g, 0.2 mole) is treated according to the procedure of Example 13B. There is obtained 5.6 g of oily residue, which is dissolved in hexane and chromatographed on silica gel (120 g). Eluding with methylene chloride gives 5.45 g (99.3%) of benzo[b]thiophene-2-carbonitrile, 3-(1-methylethoxy)-; as an oil, which is used directly in the next stage.
  • 12
  • [ 6314-42-7 ]
  • [ 106-95-6 ]
  • [ 530-62-1 ]
  • [ 104796-06-7 ]
YieldReaction ConditionsOperation in experiment
In acetonitrile 13.B Benzo[b]thiophene-2-carbonitrile, 5-methoxy-3-(1-methylethoxy)- EXAMPLE 13 (B) Benzo[b]thiophene-2-carbonitrile, 5-methoxy-3-(1-methylethoxy)- A mixture of benzo[b]thiophene-2-carboxamide, 5-methoxy-3-(1-methylethoxy) (3.25 g, 0.12 mole) and 1,1'-carbonyldiimidazole (3.96 g, 0.024 mole) in acetonitrile (220 ml) is stirred at room temperature for 80 minutes. Allylbromide (11.8 g, 0.098 mole) is added and the reaction mixture is heated at reflux for 12 hours. Most of the volatiles are removed under reduced pressure and the residue obtained is dissolved in ether and washed successively with dilute hydrochloric acid, water, aqueous sodium bicarbonate and water. The extract is dried over sodium sulfate and the solvent is removed to give 3.2 g of oily residue. The oil is purified by chromatography on silica gel (110 g). Eluding with methylene chloride gives 3.01 g (100%) of a solid, mp 80°-1° C. Recrystallization from hexane gives 2.77 g (92%) of analytically pure benzo[b]thiophene-2-carbonitrile, 5-methoxy-3-(1-methylethoxy); mp 80°-1° C.
  • 13
  • [ 4418-61-5 ]
  • [ 104796-13-6 ]
  • [ 530-62-1 ]
  • [ 6314-42-7 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In water; acetonitrile 15.F Benzo[b]thiophene-2-carboxamide, 5-methoxy-3-[(1-methylethyl) thio-N-1H-tetrazol-5-yl] EXAMPLE 15(F) Benzo[b]thiophene-2-carboxamide, 5-methoxy-3-[(1-methylethyl) thio-N-1H-tetrazol-5-yl] A mixture of benzo[b]thiophene-2-carboxylic acid, 5-methoxy-3-[(1-methylethyl)thio]- (2.5 g, 0.0085 mole) and 1,1'-carbonyldiimidazole (1.72 g, 0.011 mole) in acetonitrile (150 ml) is refluxed with stirring under nitrogen for 100 minutes. A solution of 5-aminotetrazole (0.9 g, 0.011 mole) and triethylamine (1.07 g, 0.011 mole) in acetonitrile (100 ml) is added dropwise. The mixture is heated at reflux for 17 hours, then most of the acetonitrile is removed under water aspirator pressure at 40° C. The residue is treated with cold water (~500 ml), acidified with acetic acid (3.4 ml) and stirred. The resulting solid is separated by filtration, washed with water, then with ether and dried to give 2.4 g of a solid. Recrystallization from methanol gives 1.7 g (55%) of analytically pure benzo[b]thiophene-2-carboxamide, 5-methoxy-3-[(1methylethyl)thio-N- 1H-tetrazol-5-yl]-; mp 236° C. (dec).
  • 14
  • [ 6314-42-7 ]
  • [ 534-07-6 ]
  • [ 202594-72-7 ]
YieldReaction ConditionsOperation in experiment
33% R.44 Reference Example 44 Reference Example 44 In substantially the same manner as in Reference Example 31, 2-benzo[b]thiophenecarboxamide was allowed to react with 1,3-dichloroacetone to give 2-(2-benzo[b]thienyl)-4-chloromethyloxazole. The yield was 33%. Recrystallization from ethyl acetate-hexane gave colorless prisms, mp 150-151° C.
  • 15
  • [ 90965-06-3 ]
  • [ 6314-42-7 ]
  • [ 1174216-58-0 ]
YieldReaction ConditionsOperation in experiment
52% With dirhodium(II) tetrakis(perfluorobutyramide) In toluene Reflux;
52% With dirhodium(II) tetrakis(perfluorobutyrate) In toluene for 16h; Reflux; Inert atmosphere; regioselective reaction;
  • 16
  • [ 17890-56-1 ]
  • [ 6314-42-7 ]
  • 17
  • [ 6314-42-7 ]
  • [ 6314-28-9 ]
YieldReaction ConditionsOperation in experiment
47% With acetic acid; isopentyl nitrite at 80℃; for 24h; Inert atmosphere; Benzo[b]thiophene-2-carboxylic acid (15) Benzo[b]thiophene-2-carboxamide (0.1772 g, 1 mmol)was dissolved in acetic acid (2 mL), and to the stirring solution was added amyl nitrite (0.40 mL, 3mmol). The reaction was placed under N2 atmosphere and heated to 80 °C for 24 hours, whereupon thereaction was complete by consumption of starting material by TLC. The solution was condensed andco-evaporated with toluene (2 x 5 mL), then purified via recrystallization from acetone. The resultingsuspension was filtered to afford off-white powder (0.0846 g, 0.47 mmol)
  • 18
  • [ 6314-42-7 ]
  • ethyl aminocrotonate [ No CAS ]
  • [ 4637-24-5 ]
  • ethyl 2-(benzo[b]thiophen-2-yl)-4-methylpyrimidine-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% Stage #1: benzo[b]thiophene-2-carboxamide; <i>N</i>,<i>N</i>-dimethyl-formamide dimethyl acetal In 1,2-dichloro-ethane at 60℃; Sealed tube; Stage #2: ethyl aminocrotonate With copper diacetate In 1,2-dichloro-ethane at 100℃; Molecular sieve; regioselective reaction;
  • 19
  • [ 928-49-4 ]
  • [ 6314-42-7 ]
  • 3,4-diethylbenzo[4,5]thieno[2,3-c]pyridin-1(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With potassium hexafluorophosphate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; copper diacetate; sodium acetate In toluene at 120℃; for 24h; regioselective reaction;
  • 20
  • [ 3541-37-5 ]
  • [ 6314-42-7 ]
YieldReaction ConditionsOperation in experiment
86% With ammonia; water at 120℃; Autoclave;
  • 21
  • C14H11NO3S2 [ No CAS ]
  • [ 6314-42-7 ]
  • C22H14N2O4S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydride In N,N-dimethyl-formamide; paraffin oil at 90℃;
  • 22
  • C14H11NO3S2 [ No CAS ]
  • [ 6314-42-7 ]
  • (2-(benzo[b]thiophen-2-yl)-4-(benzo[d][1,3]dioxol-6-yl)oxazol-5-yl)(thiazol-2-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydride / N,N-dimethyl-formamide; paraffin oil / 90 °C 2: iodine; tert.-butylhydroperoxide / 1,4-dioxane; water
  • 23
  • C14H10BrNO3S2 [ No CAS ]
  • [ 6314-42-7 ]
  • C23H16N2O4S3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide In toluene at 100℃; Inert atmosphere; Reflux;
  • 24
  • [ 6314-42-7 ]
  • N-(benzo[b]thiophen-2-ylmethyl)-4-nitrobenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 °C / Reflux 2: triethylamine / dichloromethane / 5 h / 0 - 20 °C
  • 25
  • [ 6314-42-7 ]
  • N-(benzo[b]thiophen-2-ylmethyl)-4-cyanobenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 °C / Reflux 2: triethylamine / dichloromethane / 5 h / 0 - 20 °C
  • 26
  • [ 6314-42-7 ]
  • N-(benzo[b]thiophen-2-ylmethyl)-4-fluorobenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 °C / Reflux 2: triethylamine / dichloromethane / 5 h / 0 - 20 °C
  • 27
  • [ 6314-42-7 ]
  • N-(benzo[b]thiophen-2-ylmethyl)-4-chlorobenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 °C / Reflux 2: triethylamine / dichloromethane / 5 h / 0 - 20 °C
  • 28
  • [ 6314-42-7 ]
  • N-(benzo[b]thiophen-2-ylmethyl)-4-bromobenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 °C / Reflux 2: triethylamine / dichloromethane / 5 h / 0 - 20 °C
  • 29
  • [ 6314-42-7 ]
  • N-(benzo[b]thiophen-2-ylmethyl)-4-(trifluoromethyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 °C / Reflux 2: triethylamine / dichloromethane / 5 h / 0 - 20 °C
  • 30
  • [ 6314-42-7 ]
  • N-(benzo[b]thiophen-2-ylmethyl)-4-methylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 °C / Reflux 2: triethylamine / dichloromethane / 5 h / 0 - 20 °C
  • 31
  • [ 6314-42-7 ]
  • N-(benzo[b]thiophen-2-ylmethyl)-2-fluorobenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 °C / Reflux 2: triethylamine / dichloromethane / 5 h / 0 - 20 °C
  • 32
  • [ 6314-42-7 ]
  • N-(benzo[b]thiophen-2-ylmethyl)-3-fluorobenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 °C / Reflux 2: triethylamine / dichloromethane / 5 h / 0 - 20 °C
  • 33
  • [ 6314-42-7 ]
  • [ 247570-04-3 ]
YieldReaction ConditionsOperation in experiment
88% Stage #1: benzo[b]thiophene-2-carboxamide With triethyl borane; phenylsilane; potassium acetate In tetrahydrofuran; tert-butyl methyl ether at 120℃; Inert atmosphere; Schlenk technique; Sealed tube; Stage #2: With hydrogenchloride In ethyl acetate at 20℃; for 8h; Inert atmosphere; chemoselective reaction;
88% Stage #1: benzo[b]thiophene-2-carboxamide With triethyl borane; phenylsilane; potassium acetate In tert-butyl methyl ether at 120℃; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube; Stage #2: With hydrogenchloride In ethyl acetate at 20℃; for 8h; Inert atmosphere; Schlenk technique; Glovebox; Sealed tube;
82% Stage #1: benzo[b]thiophene-2-carboxamide With [(aNHC)KN(SiMe3)2]2; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In toluene at 40℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; Stage #2: With water; sodium hydroxide In diethyl ether; toluene at 40℃; for 1h; Inert atmosphere; Glovebox; Schlenk technique; Stage #3: With hydrogenchloride In diethyl ether; water Inert atmosphere; Glovebox; Schlenk technique;
  • 34
  • [ 6314-42-7 ]
  • (benzo[b]thiophene-2-ylcarbonyl)sulfamoyl fluoride [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With fluorosulfonyl fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 50℃; for 12h; 4. Procedure for the synthesis of 2a-z General procedure: A mixture of amides 1 (1 mmol, 1 eq.), DBU (5 mmol, 5 equiv, 761.2 mg, 0.75 mL), and DMSO (1 mL) was allowed to stir at 50 °C under the atmosphere of a SO2F2 balloon overnight (monitored by TLC until complete consumption of amide starting materials). The reaction mixture was quenched by 2 M HCl (10 mL). Then the reaction mixture was extracted with ethyl acetate (3 × 20 mL) and the extracts were washed with water, and concentrated to dryness under reduced pressure. The residue was purified by column chromatography on silica gel using pure ethyl acetate as eluent to give the desired product (2).
  • 35
  • C20H21N3O2S [ No CAS ]
  • [ 6314-42-7 ]
  • isonicotinoyl-tert-butylformamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 70% 2: 41% With copper diacetate; palladium diacetate In water at 120℃; for 1h; Schlenk technique; Green chemistry;
  • 36
  • [ 124-38-9 ]
  • [ 6314-42-7 ]
  • N-formylbenzo[b]thiophene-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% Stage #1: benzo[b]thiophene-2-carboxamide With phenylsilane; potassium; C38H26CrN4O2(1+)*Cl(1-) In acetonitrile at 20℃; Inert atmosphere; Glovebox; Sealed tube; Stage #2: carbon dioxide In acetonitrile at 20℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube;
49% With phenylsilane; C11H13N2P In acetonitrile at 20℃; for 24h; Schlenk technique;
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