22117-85-7

Basic information

• Product Name: 2-Methoxy-5-sulfamoylbenzoic acid
• Synonyms: 2-METHOXY-5-SULFAMOYLBENZOIC ACID;2-METHOXY-5-SULFONYLBENZOIC ACID;2-METHOXY-5-SULPHAMOYLBENZOIC ACID;3-CARBOXY-4-METHOXY-BENZENE SULFONAMIDE;2-Methoxy-5-Sufamoyl Benzoic Acid;5-Aminosulfonyl-2-Methoxybenzoic Acid;5-sulphamoyl-o-anisic acid;5-(Aminosulphonyl)-2-methoxybenzoic acid
• CAS NO: 22117-85-7
• Molecular Formula: C₈H₉NO₅S
• Molecular Weight: 231.23
• EINECS: 244-789-1
• Product Categories: Organic acids;Amines, Aromatics, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals, Sulfur & Selenium Compounds
• Mol File: 22117-85-7.mol
• Article Data: 11

Chemical Properties

• Melting Point: 220 °C
• Boiling Point: 482.5 °C at 760 mmHg
• Flash Point: 245.6 °C
• Appearance: /
• Density: 1.492 g/cm³
• Vapor Pressure: 4.04E-10mmHg at 25°C
• Storage Temp.: Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 3.56±0.10(Predicted)
• CAS DataBase Reference: 2-Methoxy-5-sulfamoylbenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methoxy-5-sulfamoylbenzoic acid(22117-85-7)
• EPA Substance Registry System: 2-Methoxy-5-sulfamoylbenzoic acid(22117-85-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 22117-85-7(Hazardous Substances Data)

Usage

Uses

2-Methoxy-5-sulfamoylbenzoic Acid is a metabolite of the antipsychotic drug, Sulpiride (S689145).

InChI:InChI=1/C8H9NO5S/c1-14-7-3-2-5(15(9,12)13)4-6(7)8(10)11/h2-4H,1H3,(H,10,11)(H2,9,12,13)/p-1

Synthetic route

methyl 2-methoxy-5-sulfamoyl-benzoate (33045-52-2) → 2-methoxy-5-sulfamoylbenzoic acid (22117-85-7)

Conditions	Yield
With sodium hydroxide In methanol	98.3%
Stage #1: methyl 2-methoxy-5-sulfamoyl-benzoate With sodium hydroxide; water In methanol at 20℃; for 1h; Stage #2: With hydrogenchloride In methanol; water	98.3%
Stage #1: methyl 2-methoxy-5-sulfamoyl-benzoate With sodium hydroxide; water In methanol at 20℃; for 1h; Stage #2: With hydrogenchloride In methanol; water	98.3%

5-chlorosulfonyl-2-anisic acid (51904-91-7) → 2-methoxy-5-sulfamoylbenzoic acid (22117-85-7)

Conditions	Yield
With ammonia In tetrahydrofuran for 0.5h; Ambient temperature;	94.6%
With ammonia

2-Methoxybenzoic acid (579-75-9) → 2-methoxy-5-sulfamoylbenzoic acid (22117-85-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 84.9 percent / chlorosulfuric acid / 0.67 h / 60 - 70 °C 2: 94.6 percent / NH3 / tetrahydrofuran / 0.5 h / Ambient temperature View Scheme

3-methylpyridin-2-ylamine (1603-40-3) + 2-methoxy-5-sulfamoylbenzoic acid (22117-85-7) → C6H8N2*C8H9NO5S

Conditions	Yield
In ethanol at 20℃; for 24h;	95%

2-methoxy-5-sulfamoylbenzoic acid (22117-85-7) + copper(II) acetate monohydrate (6046-93-1) → C16H20CuN2O12S2*2H2O

Conditions	Yield
In ethanol; water at 20℃; for 72h;	70%

2-methoxy-5-sulfamoylbenzoic acid (22117-85-7) + (S)-N-[[3-[3-fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]amine (168828-90-8) → 5-(aminosulfonyl)-N-(S)-[[3-[3-fluoro-4-(morpholin-4-yl)phenyl]-2-oxooxazolidin-5-yl]methyl]-2-methoxy benzamide (1390617-37-4)

Conditions	Yield
Stage #1: 2-methoxy-5-sulfamoylbenzoic acid With chloroformic acid ethyl ester; triethylamine In dichloromethane at 0 - 20℃; for 0.5h; Stage #2: (S)-N-[[3-[3-fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]amine In dichloromethane at 0 - 20℃; for 4h;	55%

2-methoxy-5-sulfamoylbenzoic acid (22117-85-7) + 2-[4-(3-trifluoromethylphenyl)piperazin-1-yl]ethan-1-amine (27144-85-0) → N-<2-<4-(3-trifluoromethylphenyl)-1-piperazinyl>ethyl>2-methoxy-5-methyl sulfamoylbenzamide

Conditions	Yield
With triethylamine; isobutyl chloroformate In 1,4-dioxane for 6h; Ambient temperature;	40%

2-methoxy-5-sulfamoylbenzoic acid (22117-85-7) + 2--5-methoxytetralin (101403-17-2) → 2-methoxy-N-{2-[(5-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-ethyl}-5-sulfamoyl-benzamide

Conditions	Yield
With chloroformic acid ethyl ester; triethylamine In acetone at 0℃; for 2h;	32%

2-methoxy-5-sulfamoylbenzoic acid (22117-85-7) + 3,5-Bis-(trifluoromethyl)aniline (328-74-5) → N-[3,5-bis(trifluoromethyl)phenyl]-2-methoxy-5-sulfamoyl-benzamide (439146-22-2)

Conditions	Yield
	24.2%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 2-methoxy-5-sulfamoylbenzoic acid (22117-85-7) + N-hydroxysuccinimido diphenyl phosphate (75513-55-2) + N-ethyl-2-aminomethylpyrrole (74402-54-3) → N-[(1-ethyl-2-pyrrolidinyl)methyl]-2-methoxy-5-sulfamoylbenzamide (15676-16-1)

Conditions	Yield
With triethylamine In acetonitrile	24%

2-methoxy-5-sulfamoylbenzoic acid (22117-85-7) → 2-hydroxy-5-sulfonamidobenzoic acid (5378-41-6)

Conditions	Yield
With potassium hydroxide
With hydrogen bromide; acetic acid In methanol; water

1-methyl-piperazine (109-01-3) + 2-methoxy-5-sulfamoylbenzoic acid (22117-85-7) → 5-(aminosulfonyl)-2-methoxybenzoic acid 4-methylpiperazide (113681-65-5)

Conditions	Yield
With chloroformic acid ethyl ester; triethylamine 1) CH2Cl2, -5 deg C, 1 h; 2) CH2Cl2, 0 deg C, 30 min, then room temp.; Yield given. Multistep reaction;

2-tetrahydrothiophenemethylamine (83171-40-8) + 2-methoxy-5-sulfamoylbenzoic acid (22117-85-7) → N-<(2-tetrahydrothienyl)methyl>-2-methoxy-5-sulfamoylbenzamide (118894-84-1)

Conditions	Yield
With chloroformic acid ethyl ester; triethylamine 1.) acetone, 0 deg C, 30 min, 2.) acetone, 0 deg C, 30 min then r.t., 2,5 h; Yield given. Multistep reaction;

1-ethylpiperidin-3-amine (6789-94-2) + 2-methoxy-5-sulfamoylbenzoic acid (22117-85-7) → N-(1-ethyl-piperidin-3-yl)-2-methoxy-5-sulfamoyl-benzamide (51218-14-5)

Conditions	Yield
With pyridine; phosphorus trichloride 1.) RT, 1 h, 2.) from 100 deg C to 120 deg C, 4 h; Yield given. Multistep reaction;

4-amino-N-ethylpiperidine (50534-45-7) + 2-methoxy-5-sulfamoylbenzoic acid (22117-85-7) → N-(1-Ethyl-piperidin-4-yl)-2-methoxy-5-sulfamoyl-benzamide (102535-19-3)

Conditions	Yield
With pyridine; phosphorus trichloride 1.) RT, 1 h, 2.) from 100 deg C to 120 deg C, 4 h; Yield given. Multistep reaction;

1-isobutylpiperazine (5308-28-1) + 2-methoxy-5-sulfamoylbenzoic acid (22117-85-7) → 3-(4-Isobutyl-piperazine-1-carbonyl)-4-methoxy-benzenesulfonamide (102535-28-4)

Conditions	Yield
With pyridine; phosphorus trichloride 1.) RT, 1 h, 2.) from 100 deg C to 120 deg C, 4 h; Yield given. Multistep reaction;

1-phenylmethylpiperazine (2759-28-6) + 2-methoxy-5-sulfamoylbenzoic acid (22117-85-7) → 5-(aminosulfonyl)-2-methoxybenzoic acid 4-benzylpiperazide (57479-93-3)

Conditions	Yield
With chloroformic acid ethyl ester; triethylamine 1) CH2Cl2, dioxane, -10 deg C, 30 min; 2) 0 deg C, 1 h, then room temp., 8.5 h; Yield given. Multistep reaction;
With pyridine; phosphorus trichloride 1.) RT, 1 h, 2.) from 100 deg C to 120 deg C, 4 h; Yield given. Multistep reaction;

1-(4-methoxybenzyl)piperazine (21867-69-6) + 2-methoxy-5-sulfamoylbenzoic acid (22117-85-7) → 4-Methoxy-3-[4-(4-methoxy-benzyl)-piperazine-1-carbonyl]-benzenesulfonamide (102535-34-2)

Conditions	Yield
With pyridine; phosphorus trichloride 1.) RT, 1 h, 2.) from 100 deg C to 120 deg C, 4 h; Yield given. Multistep reaction;

2-methoxy-5-sulfamoylbenzoic acid (22117-85-7) + (4-benzylmorpholin-2-yl)methanamine (110859-47-7, 140646-11-3) → N-(4-Benzyl-morpholin-2-ylmethyl)-2-methoxy-5-sulfamoyl-benzamide (112887-21-5)

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 4h; Ambient temperature;

2-methoxy-5-sulfamoylbenzoic acid (22117-85-7) + 1-cyclohexylmethylpiperazine (57184-23-3) → 3-(4-Cyclohexylmethyl-piperazine-1-carbonyl)-4-methoxy-benzenesulfonamide (102535-29-5)

Conditions	Yield
With pyridine; phosphorus trichloride 1.) RT, 1 h, 2.) from 100 deg C to 120 deg C, 4 h; Yield given. Multistep reaction;

2-methoxy-5-sulfamoylbenzoic acid (22117-85-7) + 4-amino-6-azobrendane (84409-92-7) → 2-Methoxy-N-((1R,2S,3S,6S,7R)-4-methyl-4-aza-tricyclo[4.2.1.03,7]non-2-yl)-5-sulfamoyl-benzamide; compound with (E)-but-2-enedioic acid (84410-00-4)

Conditions	Yield
With chloroformic acid ethyl ester; triethylamine 1.) THF, 0 deg C, 30 min; 2.) THF, 1 h, room temp.; Yield given. Multistep reaction;

2-methoxy-5-sulfamoylbenzoic acid (22117-85-7) + (S)-octahydropyrrolo[1,2-a]pyrazine (93643-24-4) → 3-((S)-Hexahydro-pyrrolo[1,2-a]pyrazine-2-carbonyl)-4-methoxy-benzenesulfonamide (102535-38-6)

Conditions	Yield
With pyridine; phosphorus trichloride 1.) RT, 1 h, 2.) from 100 deg C to 120 deg C, 4 h; Multistep reaction;

2-methoxy-5-sulfamoylbenzoic acid (22117-85-7) + (S)-1-ethyl-2-<(N-methylamino)methyl>pyrrolidine (102535-40-0) → N-((S)-1-Ethyl-pyrrolidin-2-ylmethyl)-2-methoxy-N-methyl-5-sulfamoyl-benzamide (102535-23-9)

Conditions	Yield
With triethylamine; Diphenylphosphinic chloride 1.) THF, -10 deg C, 1 h, 2.) THF, from -10 deg C to RT, 12 h; Yield given. Multistep reaction;

2-methoxy-5-sulfamoylbenzoic acid (22117-85-7) + 2,5-dichloropentylamine hydrochloride (62922-45-6) → N-(2,5-dichloropentyl)-2-methoxy-5-sulfamoylbenzamide (67833-50-5)

Conditions	Yield
With chloroformic acid ethyl ester; triethylamine 1.) acetone, 0 deg C, 0.5 h, 2.) 0 deg C, 0.5 h then r.t., 2.5 h; Yield given. Multistep reaction;

2-methoxy-5-sulfamoylbenzoic acid (22117-85-7) → 2-methoxy-5-sulphamoyl-benzoyl chloride (52542-44-6)

Conditions	Yield
With pyridine; thionyl chloride Heating;
With thionyl chloride In N-methyl-acetamide; 1,1-dichloroethane
With thionyl chloride In tetrahydrofuran; benzene
With thionyl chloride at 105℃;

2-methoxy-5-sulfamoylbenzoic acid (22117-85-7) + chloroformic acid ethyl ester (541-41-3) → C11H13NO7S

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; triethylamine In dichloromethane at -40 - -10℃; for 0.5h;

2-methoxy-5-sulfamoylbenzoic acid (22117-85-7) + 1-allylpiperazine (13961-36-9) → 3-(4-Allyl-piperazine-1-carbonyl)-4-methoxy-benzenesulfonamide (102535-27-3)

Conditions	Yield
With pyridine; phosphorus trichloride 1.) RT, 1 h, 2.) from 100 deg C to 120 deg C, 4 h; Yield given. Multistep reaction;

2-methoxy-5-sulfamoylbenzoic acid (22117-85-7) + benzylamine (100-46-9) → N-benzyl-5-(aminosulfonyl)-2-methoxybenzamide (113681-63-3)

Conditions	Yield
With chloroformic acid ethyl ester; triethylamine 1) CH2Cl2, -5 deg C, 1 h; 2) CH2Cl2, 0 deg C, 30 min, then room temp.; Yield given. Multistep reaction;

2-methoxy-5-sulfamoylbenzoic acid (22117-85-7) + 1-(Ethoxycarbonylmethyl)piperazine (40004-08-8) → [4-(2-Methoxy-5-sulfamoyl-benzoyl)-piperazin-1-yl]-acetic acid ethyl ester (102535-31-9)

Conditions	Yield
With pyridine; phosphorus trichloride 1.) RT, 1 h, 2.) from 100 deg C to 120 deg C, 4 h; Yield given. Multistep reaction;

2-methoxy-5-sulfamoylbenzoic acid (22117-85-7) + N(2-methyl-1-butyl)piperazine (82499-91-0) → 4-Methoxy-3-[4-(2-methyl-butyl)-piperazine-1-carbonyl]-benzenesulfonamide; hydrochloride (102535-30-8)

Conditions	Yield
With pyridine; phosphorus trichloride 1.) RT, 1 h, 2.) from 100 deg C to 120 deg C, 4 h; Yield given. Multistep reaction;

2-methoxy-5-sulfamoylbenzoic acid (22117-85-7) + 1-(3-methoxy-benzyl)-piperazine (55212-32-3) → 4-Methoxy-3-[4-(3-methoxy-benzyl)-piperazine-1-carbonyl]-benzenesulfonamide (102535-35-3)

Conditions	Yield
With pyridine; phosphorus trichloride 1.) RT, 1 h, 2.) from 100 deg C to 120 deg C, 4 h; Yield given. Multistep reaction;

Upstream product

• 51904-91-7 5-chlorosulfonyl-2-anisic acid 
• 579-75-9 2-Methoxybenzoic acid 
• 33045-52-2 methyl 2-methoxy-5-sulfamoyl-benzoate 

Downstream Products

• 5378-41-6 2-hydroxy-5-sulfonamidobenzoic acid 
• 113681-65-5 5-(aminosulfonyl)-2-methoxybenzoic acid 4-methylpiperazide 
• 51218-14-5 N-(1-ethyl-piperidin-3-yl)-2-methoxy-5-sulfamoyl-benzamide 
• 102535-19-3 N-(1-Ethyl-piperidin-4-yl)-2-methoxy-5-sulfamoyl-benzamide 
• 102535-28-4 3-(4-Isobutyl-piperazine-1-carbonyl)-4-methoxy-benzenesulfonamide 
• 102535-34-2 4-Methoxy-3-[4-(4-methoxy-benzyl)-piperazine-1-carbonyl]-benzenesulfonamide 
• 102535-31-9 [4-(2-Methoxy-5-sulfamoyl-benzoyl)-piperazin-1-yl]-acetic acid ethyl ester 
• 102535-32-0 4-Methoxy-3-[4-(2-oxo-2-pyrrolidin-1-yl-ethyl)-piperazine-1-carbonyl]-benzenesulfonamide 
• 102535-20-6 N-(2-Dimethylamino-1-methyl-ethyl)-2-methoxy-5-sulfamoyl-benzamide 
• 33045-52-2 methyl 2-methoxy-5-sulfamoyl-benzoate 
• 139095-72-0 N-((S)-1-Decyl-pyrrolidin-2-ylmethyl)-2-methoxy-5-sulfamoyl-benzamide 
• 139095-43-5 N-((R)-1-Decyl-pyrrolidin-2-ylmethyl)-2-methoxy-5-sulfamoyl-benzamide 
• 139095-75-3 N-((S)-1-Dodecyl-pyrrolidin-2-ylmethyl)-2-methoxy-5-sulfamoyl-benzamide 
• 140237-05-4 N-((R)-1-Dodecyl-pyrrolidin-2-ylmethyl)-2-methoxy-5-sulfamoyl-benzamide 

Relevant articles and documents

Preparation method of 2-methoxy-5-sulfamoylbenzoic acid

The invention provides a preparation method of 2-methoxy-5-sulfamoylbenzoic acid, comprising the following steps: carrying out bromination reaction on 4-methoxybenzenesulfonamide and bromine under theaction of a reducing agent to obtain 3-bromo-4-methoxybenzenesulfonamide; carrying out substitution reaction on 3-bromo-4-methoxybenzenesulfonamide and cuprous cyanide under the action of a catalystto generate 3-cyano-4-methoxybenzenesulfonamide; carrying out alcoholysis on the 3-cyano-4-methoxybenzenesulfonamide and methanol under the catalysis of an acid to obtain 2-methoxy-5-sulfonamide methyl benzoate; hydrolyzing 2-methoxy-5-sulfonamide methyl benzoate under an alkaline condition, and then acidifying to obtain the 2-methoxy-5-sulfamoylbenzoic acid. The preparation method of the 2-methoxy-5-sulfamoylbenzoic acid is mild in reaction condition, simple in process and equipment, convenient to operate and environmentally friendly.

THERAPEUTIC AGENT FOR CANCER

A medicament for the prevention and/or treatment of cancers and the like which comprises as an active ingredient a substance selected from the group consisting of a compound represented by the following general formula (I) and a pharmacologically acceptable salt thereof, and a hydrate thereof and a solvate thereof: wherein A represents hydrogen atom or acetyl group, E represents a 2,5-di-substituted or a 3,5-di-substituted phenyl group, or a monocyclic or a fused polycyclic heteroaryl group which may be substituted, provided that the compound wherein said heteroaryl group is 1? a fused polycyclic heteroaryl group wherein the ring which binds directly to ―CONH― group in the formula (I) is a benzene ring, 2? unsubstituted thiazol-2-yl group, or 3? unsubstituted benzothiazol-2-yl group is excluded, ring Z represents an arene which may have one or more substituents in addition to the group represented by formula ―O―A wherein A has the same meaning as that defined above and the group represented by formula ―CONH―E wherein E has the same meaning as that defined above, or a heteroarene which may have one or more substituents in addition to the group represented by formula ―O―A wherein A has the same meaning as that defined above and the group represented by formula ― CONH―E wherein E has the same meaning as that defined above.

THERAPEUTIC DRUG FOR DIABETES

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