57683-71-3

Basic information

• Product Name: 2-Carbomethoxybenzenesulfonamide
• Synonyms: 2-sulfamoyl-benzoicacimethylester;Benzoic acid, 2-(aminosulfonyl)-, methyl ester;Benzoic acid, 2-sulfamoyl-, methyl ester;CARBOMETHOXYBENZENESULPHONAMIDE;METHYL 2-(AMINOSULFONYL)BENZOATE;METHYL 2-SULFAMOYLBENZOATE;METHYL 2-SULFONAMIDOBENZOATE;METHYL O-SULFAMOYLBENZOATE
• CAS NO: 57683-71-3
• Molecular Formula: C₈H₉NO₄S
• Molecular Weight: 215.23
• EINECS: 260-903-2
• Product Categories: pharmacetical;Organic Building Blocks;Sulfonamides/Sulfinamides;Sulfur Compounds
• Mol File: 57683-71-3.mol
• Article Data: 12

Chemical Properties

• Melting Point: 126-128 °C(lit.)
• Boiling Point: 401.4 °C at 760 mmHg
• Flash Point: 196.6 °C
• Appearance: Greyish crystal powder
• Density: 1.377 g/cm³
• Vapor Pressure: 1.18E-06mmHg at 25°C
• Refractive Index: 1.556
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 9.65±0.60(Predicted)
• CAS DataBase Reference: 2-Carbomethoxybenzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Carbomethoxybenzenesulfonamide(57683-71-3)
• EPA Substance Registry System: 2-Carbomethoxybenzenesulfonamide(57683-71-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• RTECS: DH6830000
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 57683-71-3(Hazardous Substances Data)

Usage

Chemical Properties

Solid

Uses

Different sources of media describe the Uses of 57683-71-3 differently. You can refer to the following data:
1. Methyl 2-(aminosulfonyl)benzoate was used in the preparation of pyrazol-benzenesulfonamides, 2-(1-phenyl-1H-pyrazol-5-yl)benzenesulfonamides.
2. Methyl 2-Sulfamoylbenzoate is a building block used in various synthetic preparations. It is also classified as a pollutant found in a municipal wastewater treatment plant.

Definition

ChEBI: A benzoate ester that is methyl benzoate substituted by a sulfamoyl group at position 2. It is a metabolite of the herbicide metsulfuron-methyl.

InChI:InChI=1/C8H9NO4S/c1-13-8(10)6-4-2-3-5-7(6)14(9,11)12/h2-5H,1H3,(H2,9,11,12)

Synthetic route

methanol (67-56-1) + saccharin (81-07-2) → methyl 2-(aminosulfonyl)benzoate (57683-71-3)

Conditions	Yield
With sulfuric acid at 10 - 70℃; for 12h; Time;	89%
With sulfuric acid In methanol for 12h; Reflux;	65%
at 170℃;

methanol (67-56-1) + 2-sulfamoyl-benzoic acid (632-24-6) → methyl 2-(aminosulfonyl)benzoate (57683-71-3)

Conditions	Yield
With sulfuric acid
With hydrogenchloride

saccharin (81-07-2) → methyl 2-(aminosulfonyl)benzoate (57683-71-3)

Conditions	Yield
With phosphorus pentachloride at 70 - 75℃; tropfenweiser Zusatz von Methylalkohol zu dem stark abgekuehlten Produkt und Kochen der ausgeschiedenen Krystalle mit Methylalkohol;

Metsulfuron-methyl (74223-64-6) → benzoic acid methyl ester (93-58-3) + methyl 2-(aminosulfonyl)benzoate (57683-71-3) + 2-(methoxycarbonyl)benzenesulfonyl isocyanate (74222-95-0) + 4-methoxy-6-methyl-1,3,5-triazin-2-amine (1668-54-8) + 2-Isocyanato-4-methoxy-6-methyl-[1,3,5]triazine + 3-(methoxy)-1,2-benzisothiazole 1,1-dioxide (18712-14-6)

Conditions	Yield
at 800℃; for 0.00138889h; Product distribution; study of the pyrolysis of various sulfonylureas; other sulfonylureas and their products;

2-methoxycarbonylbenzenesulfonyl chloride (26638-43-7) → methyl 2-(aminosulfonyl)benzoate (57683-71-3)

Conditions	Yield
With pyridine; Rink amide resin; trifluoroacetic acid 1.) CH2Cl2, room temp., 15 h, 2.) CH2Cl2, 15 min; Yield given. Multistep reaction;
With ammonium hydroxide In acetonitrile at 0 - 20℃; for 1h; Inert atmosphere;

(o-Methoxycarbonylphenylsulfonyl)carbamic acid → carbon dioxide (124-38-9) + methyl 2-(aminosulfonyl)benzoate (57683-71-3)

Conditions	Yield
With phosphoric acid In various solvent(s) at 25℃; pH=1.21; Kinetics; Activation energy; Further Variations:; pH-values; Temperatures; Reagents; Hydrolysis;

Metsulfuron-methyl (74223-64-6) → methyl 2-(aminosulfonyl)benzoate (57683-71-3) + 4-methoxy-6-methyl-1,3,5-triazin-2-amine (1668-54-8) + methyl 2-[[[[(4-hydroxy-6-methyl-1,3,5-triazine-2-yl)amino]carbonyl]amino]sulfonyl]benzoate + methyl 2-[[[[[[[(acetylamino)carbonyl]amino]carbonyl]amino]carbonyl]amino]sulfonyl]benzoate

Conditions	Yield
In water at 45℃; pH=2; Kinetics; Further Variations:; pH-values; Temperatures;

Metsulfuron-methyl (74223-64-6) → methyl 2-(aminosulfonyl)benzoate (57683-71-3) + C13H15N5O7S + 4-methoxy-6-methyl-1,3,5-triazin-2-amine (1668-54-8) + N-(carbomethoxy phenylsulfonyl)-N'-methyl urea + methyl 2-[[[[(4-hydroxy-6-methyl-1,3,5-triazine-2-yl)amino]carbonyl]amino]sulfonyl]benzoate + methyl 2-[[[[[[[(acetylamino)carbonyl]amino]carbonyl]amino]carbonyl]amino]sulfonyl]benzoate

Conditions	Yield
With HO(1-)*Fe(3+)*H2O In water pH=3.5; Irradiation;

methyl 2-(aminosulfonyl)benzoate (57683-71-3) → saccharin (81-07-2)

Conditions	Yield
With potassium hydroxide at 64℃; pH=9; Reagent/catalyst;	98.19%

methyl 2-(aminosulfonyl)benzoate (57683-71-3) + Ethyl 2-benzylacetoacetate (620-79-1) → ethyl (1,1-dioxido-1,2-benzisothiazol-3(2H)-ylidine)-2-phenyl-methyl-3-oxo-butanoate

Conditions	Yield
Stage #1: methyl 2-(aminosulfonyl)benzoate; Ethyl 2-benzylacetoacetate With N,N,N,N,-tetramethylethylenediamine; lithium diisopropyl amide In tetrahydrofuran at 0℃; for 3.5h; Stage #2: With hydrogenchloride In tetrahydrofuran	95%

methyl 2-(aminosulfonyl)benzoate (57683-71-3) + acetic anhydride (108-24-7) → methyl 2-(N-acetylsulfamoyl)benzoate

Conditions	Yield
With zinc(II) chloride at 23℃;	95%
With zinc(II) chloride at 50℃;	86%
With zinc(II) chloride at 20℃;	75%
With zinc(II) chloride at 23℃; Inert atmosphere; Schlenk technique;

ethylthioacetic acid methyl ester (2432-51-1) + methyl 2-(aminosulfonyl)benzoate (57683-71-3) → N-butyryl-2-(methoxycarbonyl)-benzenesulfonamide (1181384-71-3)

Conditions	Yield
Stage #1: methyl 2-(aminosulfonyl)benzoate With N-Bromosuccinimide; iron(II) chloride In acetonitrile at 20℃; for 0.0166667h; Stage #2: ethylthioacetic acid methyl ester In acetonitrile at 45℃; for 10h;	94%

methyl 2-(aminosulfonyl)benzoate (57683-71-3) + (E)-1-phenyl-2-(1-(p-tolyl)ethylidene)hydrazine → 2-(3-(4-methylphenyl)-1-phenyl-1H-pyrazol-5-yl)benzenesulfonamide

Conditions	Yield
Stage #1: (E)-1-phenyl-2-(1-(p-tolyl)ethylidene)hydrazine With lithium diisopropyl amide In tetrahydrofuran; hexane at 0℃; Stage #2: methyl 2-(aminosulfonyl)benzoate In tetrahydrofuran; hexane at 0℃;	93%

methyl 2-(aminosulfonyl)benzoate (57683-71-3) + chloral (75-87-6) → 2-benzoesaeuremethylester (121583-26-4)

Conditions	Yield
With hydrogenchloride for 16h; Heating;	90%

isopropyl acetoacetate (542-08-5) + methyl 2-(aminosulfonyl)benzoate (57683-71-3) → (1-methylethyl)-4-(1,1-dioxido-1,2-benzisothiazol-3(2H)-ylidine)-3-oxo-butanoate

Conditions	Yield
Stage #1: isopropyl acetoacetate With lithium diisopropyl amide In tetrahydrofuran for 1h; Stage #2: methyl 2-(aminosulfonyl)benzoate In tetrahydrofuran at 0℃; for 3h;	90%
Stage #1: isopropyl acetoacetate; methyl 2-(aminosulfonyl)benzoate With N,N,N,N,-tetramethylethylenediamine; lithium diisopropyl amide In tetrahydrofuran at 0℃; for 3.5h; Stage #2: With hydrogenchloride In tetrahydrofuran	78%

methyl 2-(aminosulfonyl)benzoate (57683-71-3) + dimethyl amine (124-40-3) → C9H12N2O3S

Conditions	Yield
In tetrahydrofuran at 10 - 25℃; for 20h;	90%

2-acetonaphthone BOC-hydrazone + methyl 2-(aminosulfonyl)benzoate (57683-71-3) → 2-(3-(2-naphthyl)-1H-pyrazol-5-yl)benzenesulfonamide (1011502-56-9)

Conditions	Yield
Stage #1: 2-acetonaphthone BOC-hydrazone; methyl 2-(aminosulfonyl)benzoate With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at 0 - 20℃; Stage #2: With hydrogenchloride In tetrahydrofuran Heating; Further stages.;	89%

methyl 2-(aminosulfonyl)benzoate (57683-71-3) + 1,5-anhydro-6-O-triisopropylsilyl-3,4-O-carbonate-2-deoxy-D-lyxo-hex-1-enopyranose (149625-80-9) → methyl 2-(N-((2R,5R,6R)-5-hydroxy-6-(((triisopropylsilyl)oxy)methyl)-5,6-dihydro-2H-pyran-2-yl)sulfamoyl)benzoate

Conditions	Yield
With palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In dichloromethane at 20℃; for 12h; Schlenk technique; Inert atmosphere; stereoselective reaction;	88%

methyl 2-(aminosulfonyl)benzoate (57683-71-3) + phenyllithium (591-51-5) → 3-phenylbenzo[d]isothiazole-1,1-dioxide (53440-57-6)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃;	87%

methyl 2-(aminosulfonyl)benzoate (57683-71-3) + 1-phenylbutan-1,3-dione (93-91-4) → 4-(1,1-dioxido-1,2-benzisothiazol-3(2H)-ylidine)-1-phenylbutan-1,3-dione

Conditions	Yield
Stage #1: 1-phenylbutan-1,3-dione With lithium diisopropyl amide In tetrahydrofuran for 1h; Stage #2: methyl 2-(aminosulfonyl)benzoate In tetrahydrofuran at 0℃; for 3h;	87%

tert-butyl acetoacetate (1694-31-1) + methyl 2-(aminosulfonyl)benzoate (57683-71-3) → 1,1-dimethylethyl (1,1-dioxido-1,2-benzisothiazol-3(2H)-ylidine)-3-oxo-butanoate

Conditions	Yield
Stage #1: tert-butyl acetoacetate; methyl 2-(aminosulfonyl)benzoate With N,N,N,N,-tetramethylethylenediamine; lithium diisopropyl amide In tetrahydrofuran at 0℃; for 3.5h; Stage #2: With hydrogenchloride In tetrahydrofuran	86%

methyl 2-(aminosulfonyl)benzoate (57683-71-3) + tert-butyldimethylsilyl chloride (18162-48-6) → methyl 2-(N-(tert-butyldimethylsilyl)sulfamoyl)benzoate

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	85%
With triethylamine In dichloromethane at 20℃; for 20h;

methyl 2-(aminosulfonyl)benzoate (57683-71-3) + methyllithium (917-54-4) → 3-methylbenzo[d]isothiazole-1,1-dioxide (34989-82-7)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃;	83%

4,6-dimethoxy-1,3,5-triazin-2-yl-carbamic acid,phenyl ester (98320-74-2) + methyl 2-(aminosulfonyl)benzoate (57683-71-3) + sodium phenoxide (139-02-6) → N-[(4,6-Dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide (74223-63-5)

Conditions	Yield
Stage #1: 4,6-dimethoxy-1,3,5-triazin-2-yl-carbamic acid,phenyl ester; methyl 2-(aminosulfonyl)benzoate; sodium phenoxide In N,N-dimethyl acetamide for 1.58333h; Stage #2: With hydrogenchloride In N,N-dimethyl acetamide; water at 0℃;	82.2%

methyl 2-(aminosulfonyl)benzoate (57683-71-3) + benzaldehyde (100-52-7) → 2-{[1-Phenyl-meth-(E)-ylidene]-sulfamoyl}-benzoic acid methyl ester

Conditions	Yield
With K 10 clay; calcium carbonate; trimethyl orthoformate at 180 - 183℃; for 0.133333h; Condensation; Irradiation;	82%

methyl 2-(aminosulfonyl)benzoate (57683-71-3) → 2-azidosulfonylbenzoic acid methyl ester (911392-01-3)

Conditions	Yield
With copper(ll) sulfate pentahydrate; sodium hydrogencarbonate; perfluorobutanesulfonyl azide In methanol; diethyl ether; water at 20℃; for 6h;	82%

methyl 2-(aminosulfonyl)benzoate (57683-71-3) + (E)-1-(1-(4-methoxyphenyl)ethylidene)-2-phenylhydrazine (117788-17-7) → 2-(3-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-5-yl)benzenesulfonamide

Conditions	Yield
Stage #1: (E)-1-(1-(4-methoxyphenyl)ethylidene)-2-phenylhydrazine With lithium diisopropyl amide In tetrahydrofuran; hexane at 0℃; Stage #2: methyl 2-(aminosulfonyl)benzoate In tetrahydrofuran; hexane at 0℃;	80%

methyl 2-(aminosulfonyl)benzoate (57683-71-3) + chloro(chlorosulfanyl)methanone (2757-23-5) → o-Carboxymethylphenylsulfonyl isocyanate + 2-(methoxycarbonyl)benzenesulfonyl isocyanate (74222-95-0)

Conditions	Yield
With pyridine; thionyl chloride	A n/a B 79%

3,6-dichloro-2-pyridinecarboxylic acid phenyl ester (324028-93-5) + methyl 2-(aminosulfonyl)benzoate (57683-71-3) → 2-[[[(3,6-Dichloropyridin-2-yl)carbonyl]-amino]sulfonyl]benzoic Acid Methyl Ester

Conditions	Yield
With potassium carbonate	77.2%

methyl 2-(aminosulfonyl)benzoate (57683-71-3) + dimethyl N-cyanodithioiminocarbonate (10191-60-3) → methyl 2-({[(cyanoimino)(methylsulfanyl)methyl]amino}sulfonyl)benzoate

Conditions	Yield
Stage #1: methyl 2-(aminosulfonyl)benzoate; dimethyl N-cyanodithioiminocarbonate With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 15h; Stage #2: With hydrogenchloride In N,N-dimethyl-formamide at 20℃; for 8h;	77%

4-(cyclopropylcarbamoyl)benzoic acid + methyl 2-(aminosulfonyl)benzoate (57683-71-3) → N1-cyclopropyl-N4-[2-(methoxycarbonyl)phenylsulfonyl]terephthalamide

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In acetonitrile at 20℃; for 24h;	77%

INDANE (496-11-7) + methyl 2-(aminosulfonyl)benzoate (57683-71-3) → 2-(indan-1-ylsulfamoyl)-benzoic acid methyl ester

Conditions	Yield
With tert.butyl-peroxyacetate; 4 A molecular sieve; copper(II) bis(trifluoromethanesulfonate); 1,10-Phenanthroline In 1,2-dichloro-ethane at 60℃; for 6h;	76%

methyl 2-(aminosulfonyl)benzoate (57683-71-3) + 4,6-dimethoxy-pyridine-2-carboxylic acid (90764-84-4) → 2-[[[(4,6-Dimethoxypyridin-2-yl)carbonyl]-amino]sulfonyl]benzoic Acid Methyl Ester (204378-19-8)

Conditions	Yield
	75.6%

1-tetralone oxime (3349-64-2, 68253-36-1, 100485-58-3) + methyl 2-(aminosulfonyl)benzoate (57683-71-3) → 1,2,3',4'-tetrahydronaphth[1,2-c]spiro[1,2-benzoisothiazole-3,3'(3a'H)-isoxazole] 1,1-dioxide (943963-87-9)

Conditions	Yield
Stage #1: 1-tetralone oxime With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; diisopropylamine In tetrahydrofuran; hexane at 0℃; Stage #2: methyl 2-(aminosulfonyl)benzoate In tetrahydrofuran; hexane at 20℃; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane Heating; Further stages.;	74%

4-methoxyacetophenone oxime (2475-92-5) + methyl 2-(aminosulfonyl)benzoate (57683-71-3) → 3'-(4-methoxyphenyl)spiro[1,2-benzoisothiazole-3,5'(4'H)-isoxazole] 1,1-dioxide (943963-85-7)

Conditions	Yield
Stage #1: 4-methoxyacetophenone oxime With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; diisopropylamine In tetrahydrofuran; hexane at 0℃; Stage #2: methyl 2-(aminosulfonyl)benzoate In tetrahydrofuran; hexane at 20℃; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane Heating; Further stages.;	74%

methyl 2-(aminosulfonyl)benzoate (57683-71-3) + acetophenone phenylhydrazone (59130-82-4) → 2-(1,3-diphenyl-1H-pyrazol-5-yl)benzenesulfonamide

Conditions	Yield
Stage #1: acetophenone phenylhydrazone With lithium diisopropyl amide In tetrahydrofuran; hexane at 0℃; Stage #2: methyl 2-(aminosulfonyl)benzoate In tetrahydrofuran; hexane at 0℃;	73%

diazoacetic acid ethyl ester (623-73-4) + methyl 2-(aminosulfonyl)benzoate (57683-71-3) + acetonitrile (75-05-8) → diethyl 2,2'-((1-(((2-(methoxycarbonyl)phenyl)sulfonyl)imino)ethyl)azanediyl)(E)-diacetate

Conditions	Yield
With copper(II) bis(trifluoromethanesulfonate) at 80℃; for 2h;	73%

Upstream product

• 67-56-1 methanol 
• 81-07-2 saccharin 
• 119300-80-0 2-methoxycarbonyl-benzenesulfinic acid 
• 134-20-3 2-carbomethoxyaniline 
• 26638-43-7 2-methoxycarbonylbenzenesulfonyl chloride 
• 74223-64-6 Metsulfuron-methyl 
• 632-24-6 2-sulfamoyl-benzoic acid 

Downstream Products

• 567-19-1 3-chloro-1,2-benzisothiazole 1,1-dioxide 
• 79672-26-7 methyl 2-<(dimethylamino)sulfonyl>benzoate 
• 745761-41-5 N-(2-methoxycarbonylphenylsulfonyl)-1,5-dimethylpyrazole-3-carboxamide 
• 140617-83-0 methyl 2-{[(tert-butoxycarbonyl)amino]sulfonyl}benzoate 
• 74223-63-5 N-[(4,6-Dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide 
• 951762-73-5 C₁₅H₁₂NSO₄Cl 
• 951762-75-7 2-[(4-methoxybenzylidene)sulfamoyl]benzoic acid methyl ester 
• 951762-80-4 2-[(4-methylbenzylidene)sulfamoyl]benzoic acid methyl ester 

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