Conditions | Yield |
---|---|
With sulfuric acid at 10 - 70℃; for 12h; Time; | 89% |
With sulfuric acid In methanol for 12h; Reflux; | 65% |
at 170℃; |
Conditions | Yield |
---|---|
With sulfuric acid | |
With hydrogenchloride |
saccharin
methyl 2-(aminosulfonyl)benzoate
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
A
benzoic acid methyl ester
B
methyl 2-(aminosulfonyl)benzoate
C
2-(methoxycarbonyl)benzenesulfonyl isocyanate
D
4-methoxy-6-methyl-1,3,5-triazin-2-amine
F
3-(methoxy)-1,2-benzisothiazole 1,1-dioxide
Conditions | Yield |
---|---|
at 800℃; for 0.00138889h; Product distribution; study of the pyrolysis of various sulfonylureas; other sulfonylureas and their products; |
2-methoxycarbonylbenzenesulfonyl chloride
methyl 2-(aminosulfonyl)benzoate
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; |
A
carbon dioxide
B
methyl 2-(aminosulfonyl)benzoate
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
A
methyl 2-(aminosulfonyl)benzoate
B
4-methoxy-6-methyl-1,3,5-triazin-2-amine
Conditions | Yield |
---|---|
In water at 45℃; pH=2; Kinetics; Further Variations:; pH-values; Temperatures; |
Metsulfuron-methyl
A
methyl 2-(aminosulfonyl)benzoate
C
4-methoxy-6-methyl-1,3,5-triazin-2-amine
Conditions | Yield |
---|---|
With HO(1-)*Fe(3+)*H2O In water pH=3.5; Irradiation; |
methyl 2-(aminosulfonyl)benzoate
saccharin
Conditions | Yield |
---|---|
With potassium hydroxide at 64℃; pH=9; Reagent/catalyst; | 98.19% |
methyl 2-(aminosulfonyl)benzoate
Ethyl 2-benzylacetoacetate
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
acetic anhydride
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
methyl 2-(aminosulfonyl)benzoate
N-butyryl-2-(methoxycarbonyl)-benzenesulfonamide
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
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% |
Conditions | Yield |
---|---|
With hydrogenchloride for 16h; Heating; | 90% |
isopropyl acetoacetate
methyl 2-(aminosulfonyl)benzoate
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% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 10 - 25℃; for 20h; | 90% |
methyl 2-(aminosulfonyl)benzoate
2-(3-(2-naphthyl)-1H-pyrazol-5-yl)benzenesulfonamide
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
1,5-anhydro-6-O-triisopropylsilyl-3,4-O-carbonate-2-deoxy-D-lyxo-hex-1-enopyranose
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
phenyllithium
3-phenylbenzo[d]isothiazole-1,1-dioxide
Conditions | Yield |
---|---|
In tetrahydrofuran at 0 - 20℃; | 87% |
methyl 2-(aminosulfonyl)benzoate
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
methyl 2-(aminosulfonyl)benzoate
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
tert-butyldimethylsilyl chloride
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; | 85% |
With triethylamine In dichloromethane at 20℃; for 20h; |
methyl 2-(aminosulfonyl)benzoate
methyllithium
3-methylbenzo[d]isothiazole-1,1-dioxide
Conditions | Yield |
---|---|
In tetrahydrofuran at 0 - 20℃; | 83% |
4,6-dimethoxy-1,3,5-triazin-2-yl-carbamic acid,phenyl ester
methyl 2-(aminosulfonyl)benzoate
sodium phenoxide
N-[(4,6-Dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide
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
benzaldehyde
Conditions | Yield |
---|---|
With K 10 clay; calcium carbonate; trimethyl orthoformate at 180 - 183℃; for 0.133333h; Condensation; Irradiation; | 82% |
methyl 2-(aminosulfonyl)benzoate
2-azidosulfonylbenzoic acid methyl ester
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
(E)-1-(1-(4-methoxyphenyl)ethylidene)-2-phenylhydrazine
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
chloro(chlorosulfanyl)methanone
B
2-(methoxycarbonyl)benzenesulfonyl isocyanate
Conditions | Yield |
---|---|
With pyridine; thionyl chloride | A n/a B 79% |
3,6-dichloro-2-pyridinecarboxylic acid phenyl ester
methyl 2-(aminosulfonyl)benzoate
Conditions | Yield |
---|---|
With potassium carbonate | 77.2% |
methyl 2-(aminosulfonyl)benzoate
dimethyl N-cyanodithioiminocarbonate
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% |
methyl 2-(aminosulfonyl)benzoate
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In acetonitrile at 20℃; for 24h; | 77% |
INDANE
methyl 2-(aminosulfonyl)benzoate
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
4,6-dimethoxy-pyridine-2-carboxylic acid
2-[[[(4,6-Dimethoxypyridin-2-yl)carbonyl]-amino]sulfonyl]benzoic Acid Methyl Ester
Conditions | Yield |
---|---|
75.6% |
1-tetralone oxime
methyl 2-(aminosulfonyl)benzoate
1,2,3',4'-tetrahydronaphth[1,2-c]spiro[1,2-benzoisothiazole-3,3'(3a'H)-isoxazole] 1,1-dioxide
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
methyl 2-(aminosulfonyl)benzoate
3'-(4-methoxyphenyl)spiro[1,2-benzoisothiazole-3,5'(4'H)-isoxazole] 1,1-dioxide
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
acetophenone phenylhydrazone
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
methyl 2-(aminosulfonyl)benzoate
acetonitrile
Conditions | Yield |
---|---|
With copper(II) bis(trifluoromethanesulfonate) at 80℃; for 2h; | 73% |
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