5-chloro-2-methoxy-N-(4-sulfamoylphenethyl)benzamide
Cyclohexyl isocyanate
Glibenclamid
Conditions | Yield |
---|---|
With copper(l) chloride In nitromethane at 20℃; for 2h; Reagent/catalyst; Solvent; Concentration; Milling; | 100 %Spectr. |
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 0.166667h; Sealed tube; | 81 mg |
With 18-crown-6 ether; potassium tert-butylate In N,N-dimethyl-formamide at 0 - 5℃; for 6h; Reflux; | 4.49 g |
Conditions | Yield |
---|---|
With palladium diacetate In acetonitrile at 20℃; under 15 Torr; Schlenk technique; Sealed tube; | 99% |
Glibenclamid
Conditions | Yield |
---|---|
In toluene at 110℃; Industrial scale; |
5-chloro-2-methoxybenzoic acid
Glibenclamid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: oxalyl dichloride / dichloromethane / 12 h / 20 °C / Schlenk technique 2: triethylamine / dichloromethane / 6 h / 20 °C / Schlenk technique 3: palladium diacetate / acetonitrile / 20 °C / 15 Torr / Schlenk technique; Sealed tube View Scheme | |
Multi-step reaction with 5 steps 1: oxalyl dichloride / dichloromethane / 12 h / 20 °C / Schlenk technique 2: triethylamine / dichloromethane / 6 h / 20 °C / Schlenk technique 3: chlorosulfonic acid / 1,2-dichloro-ethane / 50 °C / Schlenk technique 4: sodium azide / acetonitrile / 50 °C / Schlenk technique 5: palladium diacetate / acetonitrile / 20 °C / 15 Torr / Schlenk technique; Sealed tube View Scheme | |
Multi-step reaction with 4 steps 1: phosphorus trichloride / tetrahydrofuran / 0.08 h / 150 °C / Sealed tube 2: chlorosulfonic acid / chloroform / 0.17 h / 60 °C / Sealed tube 3: ammonium hydroxide / 1,4-dioxane / 0.17 h / 120 °C / Sealed tube; Cooling with ice 4: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Sealed tube View Scheme |
DK13
Glibenclamid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: chlorosulfonic acid / 1,2-dichloro-ethane / 50 °C / Schlenk technique 2: sodium azide / acetonitrile / 50 °C / Schlenk technique 3: palladium diacetate / acetonitrile / 20 °C / 15 Torr / Schlenk technique; Sealed tube View Scheme | |
Multi-step reaction with 3 steps 1: chlorosulfonic acid / chloroform / 0.17 h / 60 °C / Sealed tube 2: ammonium hydroxide / 1,4-dioxane / 0.17 h / 120 °C / Sealed tube; Cooling with ice 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Sealed tube View Scheme |
phenethylamine
Glibenclamid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: phosphorus trichloride / tetrahydrofuran / 0.08 h / 150 °C / Sealed tube 2: chlorosulfonic acid / chloroform / 0.17 h / 60 °C / Sealed tube 3: ammonium hydroxide / 1,4-dioxane / 0.17 h / 120 °C / Sealed tube; Cooling with ice 4: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Sealed tube View Scheme | |
Multi-step reaction with 5 steps 1.1: pyridine / tetrahydrofuran / 4 h / 20 °C / Cooling with ice 2.1: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice 3.1: ammonium hydroxide / acetone / 20 °C 4.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere 4.2: 16 h / 20 °C 5.1: potassium tert-butylate; 18-crown-6 ether / N,N-dimethyl-formamide / 6 h / 0 - 5 °C / Reflux View Scheme |
2-methoxy-5-chlorobenzoyl chloride
Glibenclamid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 6 h / 20 °C / Schlenk technique 2: palladium diacetate / acetonitrile / 20 °C / 15 Torr / Schlenk technique; Sealed tube View Scheme | |
Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 6 h / 20 °C / Schlenk technique 2: chlorosulfonic acid / 1,2-dichloro-ethane / 50 °C / Schlenk technique 3: sodium azide / acetonitrile / 50 °C / Schlenk technique 4: palladium diacetate / acetonitrile / 20 °C / 15 Torr / Schlenk technique; Sealed tube View Scheme |
4-(2-[(5-chloro-2-methoxyphenyl)formamido]ethyl)benzene-1-sulfonyl chloride
Glibenclamid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium azide / acetonitrile / 50 °C / Schlenk technique 2: palladium diacetate / acetonitrile / 20 °C / 15 Torr / Schlenk technique; Sealed tube View Scheme |
5-chloro-2-methoxy-N-(4-sulfamoylphenethyl)benzamide
Glibenclamid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: ammonium hydroxide / acetone / Industrial scale 2.1: pyrographite / acetone / 1.17 h / Reflux; Industrial scale 2.2: 0.5 h / 58 °C / Industrial scale 3.1: toluene / 110 °C / Industrial scale View Scheme |
2,2,2-trifluoro-N-(2-phenylethyl)acetamide
Glibenclamid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice 2.1: ammonium hydroxide / acetone / 20 °C 3.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere 3.2: 16 h / 20 °C 4.1: potassium tert-butylate; 18-crown-6 ether / N,N-dimethyl-formamide / 6 h / 0 - 5 °C / Reflux View Scheme |
4-[2-(2,2,2-trifluoroacetamido)ethyl]benzenesulfonyl chloride
Glibenclamid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: ammonium hydroxide / acetone / 20 °C 2.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere 2.2: 16 h / 20 °C 3.1: potassium tert-butylate; 18-crown-6 ether / N,N-dimethyl-formamide / 6 h / 0 - 5 °C / Reflux View Scheme |
Conditions | Yield |
---|---|
at 25℃; pH=7; aq. phosphate buffer; |
Glibenclamid
tetra(n-butyl)ammonium hydroxide
Conditions | Yield |
---|---|
In methanol | 100% |
Glibenclamid
Conditions | Yield |
---|---|
With [(1,5-cyclooctadiene)Ir(1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene)(PPh3)]PF6; deuterium In dichloromethane at 20℃; for 2h; Sealed tube; | 100% |
With deuterium at 100℃; Sealed tube; |
Glibenclamid
Conditions | Yield |
---|---|
With Kerr's catalyst; deuterium In chlorobenzene at 120℃; for 1h; Reagent/catalyst; Temperature; | 90% |
Glibenclamid
acetic anhydride
Conditions | Yield |
---|---|
With pyridine for 0.25h; | 84% |
diethylenetriaminepentaacetic dianhydride
Glibenclamid
DTPA-glyburide
Conditions | Yield |
---|---|
Stage #1: Glibenclamid With sodium amide In dimethyl sulfoxide at 20℃; for 0.166667h; Stage #2: diethylenetriaminepentaacetic dianhydride With sodium amide In dimethyl sulfoxide for 22h; | 80% |
Conditions | Yield |
---|---|
With C17H24N5Ru(1+)*F6P(1-); Potassium benzoate; potassium carbonate In 1-methyl-pyrrolidin-2-one at 50℃; for 72h; Inert atmosphere; | 78% |
With C17H24N5Ru(1+)*F6P(1-); Potassium benzoate; potassium carbonate In 1-methyl-pyrrolidin-2-one at 50℃; for 72h; Inert atmosphere; Glovebox; | 78% |
Conditions | Yield |
---|---|
In ethanol; water addn. of hot soln. (60°C) of CuCl2*2H2O in EtOH-H2O mixt. (1:1) to hot soln. (60°C) of MeOC6H3(Cl)CONHCH2CH2C6H4SO2NHCONHC6H11 in the same solvent; stirring under reflux for 1 h; pptn., filtration, washing several times with 1:1 EtOH:H2O mixt. and then with Et2O; elem. anal.; | 76% |
Conditions | Yield |
---|---|
Reflux; | 76% |
Conditions | Yield |
---|---|
In ethanol; water addn. of hot soln. (60°C) of NiCl2*6H2O in EtOH-H2O mixt. (1:1) to hot soln. (60°C) of MeOC6H3(Cl)CONHCH2CH2C6H4SO2NHCONHC6H11 in the same solvent; stirring under reflux for 1 h; pptn., filtration, washing several times with 1:1 EtOH:H2O mixt. and then with Et2O; elem. anal.; | 74% |
Conditions | Yield |
---|---|
In ethanol; water addn. of hot soln. (60°C) of MnCl2 in EtOH-H2O mixt. (1:1) to hotsoln. (60°C) of MeOC6H3(Cl)CONHCH2CH2C6H4SO2NHCONHC6H11 in the s ame solvent; stirring under reflux for 1 h; pptn., filtration, washing several times with 1:1 EtOH:H2O mixt. and then with Et2O; elem. anal.; | 73% |
Conditions | Yield |
---|---|
With potassium phosphate monohydrate; palladium diacetate; N2Phos In water at 60℃; for 24h; Reagent/catalyst; Suzuki-Miyaura Coupling; | 73% |
Conditions | Yield |
---|---|
In ethanol; water addn. of hot soln. (60°C) of CrCl3*6H2O in EtOH-H2O mixt. (1:1) to hot soln. (60°C) of MeOC6H3(Cl)CONHCH2CH2C6H4SO2NHCONHC6H11 in the same solvent; stirring under reflux for 1 h; pptn., filtration, washing several times with 1:1 EtOH:H2O mixt. and with Et2O; elem. anal.; | 70% |
Conditions | Yield |
---|---|
In ethanol; water addn. of hot soln. (60°C) of FeCl3*6H2O in EtOH-H2O mixt. (1:1) to hot soln. (60°C) of MeOC6H3(Cl)CONHCH2CH2C6H4SO2NHCONHC6H11 in the same solvent; stirring under reflux for 1 h; pptn., filtration, washing several times with 1:1 EtOH:H2O mixt. and then with Et2O; elem. anal.; | 68% |
Conditions | Yield |
---|---|
In ethanol; water addn. of hot soln. (60°C) of ZnCl2 in EtOH-H2O mixt. (1:1) to hotsoln. (60°C) of MeOC6H3(Cl)CONHCH2CH2C6H4SO2NHCONHC6H11 in the s ame solvent; stirring under reflux for 1 h; pptn., filtration, washing several times with 1:1 EtOH:H2O mixt. and then with Et2O; elem. anal.; | 65% |
Conditions | Yield |
---|---|
In ethanol; water addn. of hot soln. (60°C) of CoCl2 in EtOH-H2O mixt. (1:1) to hotsoln. (60°C) of MeOC6H3(Cl)CONHCH2CH2C6H4SO2NHCONHC6H11 in the s ame solvent; stirring under reflux for 1 h; pptn., filtration, washing several times with 1:1 EtOH:H2O mixt. and then with Et2O; elem. anal.; | 65% |
Conditions | Yield |
---|---|
With 2,6-di(t-butyl)-4-phenylphenol; caesium carbonate In dimethyl sulfoxide at 20℃; for 20h; Irradiation; Inert atmosphere; | 61% |
Glibenclamid
N-[2-(4-[N-(cyclohexylcarbamoyl)-sulfamoyl]-phenyl)-ethyl]-5-hydroxy-2-methoxybenzamide
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol at 20℃; for 24h; | 60% |
Conditions | Yield |
---|---|
With O4P(3-)*3K(1+)*5H2O; tris(1-adamantyl)phosphine; C28H26N2O8Pd2S2 In tetrahydrofuran at 100℃; for 5h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; | 37% |
With 1,2,3-trimethoxybenzene; O4P(3-)*3K(1+)*5H2O; tris(1-adamantyl)phosphine; {2-[((acetyl-κO)amino)phenyl-κC](tri-1-adamantylphosphine)palladium}(p-toluenesulfonate) In tetrahydrofuran at 100℃; for 5h; Suzuki-Miyaura Coupling; Inert atmosphere; | 37% |
phthalic anhydride
Glibenclamid
A
N-cyclohexylphthalimide
B
5-chloro-2-methoxy-N-(4-sulfamoylphenethyl)benzamide
Conditions | Yield |
---|---|
With pyridine; dmap for 4h; Heating; | A 34% B 29% |
Glibenclamid
A
N-cyclohexylphthalimide
B
5-chloro-2-methoxy-N-(4-sulfamoylphenethyl)benzamide
Conditions | Yield |
---|---|
With pyridine; dmap; phthalic anhydride for 4h; Heating; | A 34% B 29% |
Glibenclamid
Conditions | Yield |
---|---|
Stage #1: Glibenclamid With sulfuric acid; nitric acid In 1,4-dioxane at 0 - 20℃; for 1.5h; Cooling with ice; Stage #2: Sonication; | 11% |
With sulfuric acid; nitric acid In 1,4-dioxane at 0 - 20℃; for 1.5h; | 11% |
Glibenclamid
Conditions | Yield |
---|---|
With tritium; [Ir(1,5-COD)(P(C6H5)3)2]BF4 In dichloromethane for 16h; Ambient temperature; |
Glibenclamid
N-{4-[β-(2-hydroxy-5-chlorobenzene carboxamido)ethyl]benzene-sulfonyl}-N'-cyclohexylurea
Conditions | Yield |
---|---|
With boron tribromide |
Glibenclamid
2-amino-2-hydroxymethyl-1,3-propanediol
C4H11NO3*C23H28ClN3O5S
Conditions | Yield |
---|---|
In methanol at 5℃; |
The Glyburide has the cas register number 10238-21-8, and it is a kind of white crystalline powder. The IUPAC name and systematic name are the same which is 5-chloro-N-[2-[4-(cyclohexylcarbamoylsulfamoyl)phenyl]ethyl]-2-methoxybenzamide. This chemical is insoluble in water while slightly soluble in ethanol, acetone, chloroform, and its product categories are including Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; Organics; Amino Acids & Derivatis; Isotope Labeled Compounds; API's; Potassium channel; Ion Channels. When you neee to store it, keep it in a dry, cool and well-ventilated storeroom.
The physical properties of this chemical are as follows: (1)ACD/LogP: 3.75; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.58; (4)ACD/LogD (pH 7.4): 1.79; (5)ACD/BCF (pH 5.5): 27.82; (6)ACD/BCF (pH 7.4): 4.52; (7)ACD/KOC (pH 5.5): 173.93; (8)ACD/KOC (pH 7.4): 28.24; (9)#H bond acceptors: 8; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 95.61; (13)Index of Refraction: 1.616; (14)Molar Refractivity: 126.9 cm3; (15)Molar Volume: 362.9 cm3; (16)Polarizability: 50.3×10-24 cm3; (17)Surface Tension: 61.2 dyne/cm; (18)Density: 1.36 g/cm3; (19)Exact Mass: 493.143819; (20)MonoIsotopic Mass: 493.143819; (21)Topological Polar Surface Area: 122; (22)Heavy Atom Count: 33; (23)Formal Charge: 0; (24)Complexity: 746.
As to its usage, it is usually applied in pharmaceutics. It could be used as the hypoglycemicagent, with better curative effect than tolbutamide; It is often used in the curing of mild and moderate non-insulin-dependent diabetes mellitus.
When you are dealing with this kind of chemical, you should be much more careful and then take some measures to protect yourself. Being a kind of harmful chemical, it may cause damage to health. And if by inhalation, in contact with skin and if swallowed, you will be hurt by this chemical. Therefore, you should take the following instructions. Wear suitable protective clothing, gloves and eye/face protection while using and then do not breathe dust.
In addition, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: COC1=C(C=C(C=C1)Cl)C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)NC(=O)NC3CCCCC3
(2)InChI: InChI=1S/C23H28ClN3O5S/c1-32-21-12-9-17(24)15-20(21)22(28)25-14-13-16-7-
10-19(11-8-16)33(30,31)27-23(29)26-18-5-3-2-4-6-18/h7-12,15,18H,2-6,13-14H2,1H3,(H,25,28)(H2,26,27,29)
(3)InChIKey: ZNNLBTZKUZBEKO-UHFFFAOYSA-N
Below are the toxicity information of this chemical:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LD50 | oral | > 10gm/kg (10000mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 1404, 1969. | |
guinea pig | LD50 | oral | > 15gm/kg (15000mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 1404, 1969. | |
man | TDLo | oral | 209mg/kg/4Y-I (209mg/kg) | GASTROINTESTINAL: NAUSEA OR VOMITING LIVER: "JAUNDICE, CHOLESTATIC" LIVER: OTHER CHANGES | Western Journal of Medicine. Vol. 168, Pg. 274, 1998. |
mouse | LD50 | intraperitoneal | 2700mg/kg (2700mg/kg) | Pharmaceutical Chemistry Journal Vol. 29, Pg. 265, 1995. | |
mouse | LD50 | oral | 3250mg/kg (3250mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 1640, 1966. | |
mouse | LD50 | subcutaneous | > 20gm/kg (20000mg/kg) | SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" | Oyo Yakuri. Pharmacometrics. Vol. 4, Pg. 247, 1970. |
rabbit | LD | oral | > 20gm/kg (20000mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Oyo Yakuri. Pharmacometrics. Vol. 4, Pg. 247, 1970. |
rat | LD50 | intraperitoneal | 3750mg/kg (3750mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 1413, 1969. |
rat | LD50 | oral | > 20gm/kg (20000mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 1413, 1969. | |
rat | LD50 | subcutaneous | > 20gm/kg (20000mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 1413, 1969. | |
women | TDLo | oral | 147ug/kg (0.147mg/kg) | BEHAVIORAL: COMA ENDOCRINE: HYPOGLYCEMIA | Drug Intelligence and Clinical Pharmacy. Vol. 18, Pg. 142, 1984. |
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