5577-13-9

Basic information

• Product Name: Ethyl N-(4-methylphenyl)sulfonylcarbamate
• Synonyms: ethyl n-(4-methylphenyl)sulfonylcarbamate;Ethyl [(4-methylphenyl)sulphonyl]carbamate;N-(p-Tolylsulfonyl)carbamic acid ethyl ester;Tosylcarbamic acid ethyl ester;N-(4-methylphenyl)sulfonylcarbamic acid ethyl ester;ethyl tosylcarbaMate;Gliclazide IMpurity C;Tosylurethane
• CAS NO: 5577-13-9
• Molecular Formula: C₁₀H₁₃NO₄S
• Molecular Weight: 243.28
• EINECS: 226-952-9
• Mol File: 5577-13-9.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 272℃ at 100.8-101kPa
• Appearance: /
• Density: 1.261 g/cm³
• Vapor Pressure: 1.8-7.9Pa at 20-25℃
• Refractive Index: 1.53
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• CAS DataBase Reference: Ethyl N-(4-methylphenyl)sulfonylcarbamate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl N-(4-methylphenyl)sulfonylcarbamate(5577-13-9)
• EPA Substance Registry System: Ethyl N-(4-methylphenyl)sulfonylcarbamate(5577-13-9)

Safety Data

• Hazardous Substances Data: 5577-13-9(Hazardous Substances Data)

Usage

Uses

Tosylurethane (Gliclazide EP Impurity C) is an intermediate in the synthesis of Gliclazide (G409877), a sulfonylurea hypoglycemic agent. Used as an antidiabetic.

InChI:InChI=1/C10H13NO4S/c1-3-15-10(12)11-16(13,14)9-6-4-8(2)5-7-9/h4-7H,3H2,1-2H3,(H,11,12)

Synthetic route

4-toluenesulfonyl azide (941-55-9) + ethanol (64-17-5) + carbon monoxide (201230-82-2) → Tosylurethane (5577-13-9)

Conditions	Yield
With palladium diacetate In acetonitrile at 20℃; under 15 Torr; for 12h; Schlenk technique; Sealed tube;	94%

N,N'-carbonyl-bis(4-methylbenzenesulfonamide) (5219-81-8) + Diethyl carbonate (105-58-8) → Tosylurethane (5577-13-9)

Conditions	Yield
With silica gel-supported lanthanum(III) oxide at 150℃; for 10h; Autoclave; Inert atmosphere;	90%

chloroformic acid ethyl ester (541-41-3) + toluene-4-sulfonamide (70-55-3) → Tosylurethane (5577-13-9)

Conditions	Yield
With potassium carbonate In acetone for 4h; Reflux;	87%
With sodium hydroxide

ethanol (64-17-5) + n-butyl tosylcarbamate (31224-37-0) → Tosylurethane (5577-13-9)

Conditions	Yield
at 120℃; for 0.333333h; Sealed tube; Microwave irradiation;	84%

toluene-4-sulfonamide (70-55-3) + Hexamethylphosphorous triamide (1608-26-0) → Tosylurethane (5577-13-9)

Conditions	Yield
With diethylazodicarboxylate In tetrahydrofuran for 2h; Ambient temperature;	33%

p-Toluol-(-N-carbethoxy)-iminosulfonsaeurechlorid (93506-31-1) → Tosylurethane (5577-13-9)

Conditions	Yield
With potassium hydroxide

4-methylbenzenesulfinyl chloride (10439-23-3) → Tosylurethane (5577-13-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: benzene 2: aq. KOH View Scheme

Tosyl isocyanate (4083-64-1) → Tosylurethane (5577-13-9)

methyl tosylcarbamate (14437-03-7) → Tosylurethane (5577-13-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 0.33 h / 120 °C / Sealed tube; Microwave irradiation 2: 0.33 h / 120 °C / Sealed tube; Microwave irradiation View Scheme

toluene-4-sulfonamide (70-55-3) → Tosylurethane (5577-13-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 0.17 h / 0 °C 1.2: 2.5 h / 0 - 20 °C 2.1: 0.33 h / 120 °C / Sealed tube; Microwave irradiation 3.1: 0.33 h / 120 °C / Sealed tube; Microwave irradiation View Scheme
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 0.17 h / 0 °C 1.2: 2.5 h / 0 - 20 °C 2.1: 0.33 h / 120 °C / Sealed tube; Microwave irradiation 3.1: 0.33 h / 120 °C / Sealed tube; Microwave irradiation View Scheme

→ Tosylurethane

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium azide / water; acetonitrile / 0.33 h / 20 °C / Schlenk technique 2: palladium diacetate / acetonitrile / 12 h / 20 °C / 15 Torr / Schlenk technique; Sealed tube View Scheme

Tosylurethane (5577-13-9) + 1-butyn-4-ol (927-74-2) → O-ehtyl-N-but-3-ynyl-N-(4-methylphenyl)sulfonylcarbamate (349451-03-2)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 16h;	96%

Tosylurethane (5577-13-9) + 1,1-Diphenylhydrazine (530-50-7) → 1,1-Diphenyl-4-(4-tosyl)semicarbazid

Conditions	Yield
at 130℃; for 2h;	88%

Tosylurethane (5577-13-9) + 7-amino-1,3,5-triazaadamantane (14707-75-6) → N-(p-toluenesulfonyl)-N'-[7-(1,3,5-triazaadamantyl)]urea

Conditions	Yield
In toluene for 10h; Substitution; Heating;	79.9%

Tosylurethane (5577-13-9) + tert-butyl (1-(4-chlorophenyl)-2-methylene-3-oxobutyl) carbonate (1308286-01-2) → ethyl 1-(4-chlorophenyl)-2-methylene-3-oxobutyl(tosyl)carbamate (1330174-11-2)

Conditions	Yield
With 6'-N-phenylformamide-β-ICD In tetrahydrofuran at 20℃; for 72h; optical yield given as %ee;	78%

Tosylurethane (5577-13-9) → glycyclamide (664-95-9)

Conditions	Yield
In toluene for 6h; Reflux;	75%

Tosylurethane (5577-13-9) + tert-butyl (2-methylene-3-oxo-1-(p-tolyl)butyl) carbonate (1304688-64-9) → ethyl 2-methylene-3-oxo-1-p-tolylbutyl(tosyl)carbamate (1330174-12-3)

Conditions	Yield
With 6'-N-phenylformamide-β-ICD In tetrahydrofuran at 20℃; for 72h; optical yield given as %ee;	72%

Tosylurethane (5577-13-9) → 4-p-Tolylsulfonylsemicarbazid (18258-96-3)

Conditions	Yield
With hydrazine hydrate In ethanol Heating;	71%
With hydrazine hydrate In ethanol for 8h; Heating;

Tosylurethane (5577-13-9) + 2-(6-aminopyridin-3-yl)-4-(morpholin-4-yl)-7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidine 6,6-dioxide → 4-methyl-N-((5-(4-(morpholin-4-yl)-6,6-dioxido-7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidin-2-yl)pyridin-2-yl)carbamoyl)benzenesulfonamide

Conditions	Yield
In toluene	65.3%

Tosylurethane (5577-13-9) + 4-(4-amino-2-fluorophenoxy)-N-methylpicolinamide (757251-42-6) → 4-(4-(3-(4-methylbenzenesulfonyl)ureido)-2-fluorophenoxy)-N-methylpyridine-2-carboxamide

Conditions	Yield
In toluene for 6h; Reflux;	45.3%

Tosylurethane (5577-13-9) + 4"-epi-amino-4"-deoxyavermectin B1a → C56H80N2O16S

Conditions	Yield
Reflux;	40%

Tosylurethane (5577-13-9) + 2-methoxyethylamine (109-85-3)

Conditions	Yield
With 2-methoxy-ethanol

Tosylurethane (5577-13-9) + 3,3-dimethylallylamine (13822-06-5, 108963-90-2) → 4-methyl-N-{[(3-methyl-2-butenyl)amino]carbonyl}-benzenesulfonamide (25799-83-1)

Tosylurethane (5577-13-9) → 3-Methyl-but-2-enoic acid (toluene-4-sulfonylaminocarbonyl)-amide (28490-61-1)

Tosylurethane (5577-13-9) + 4-Methyl-3-pentenamide (70265-05-3) → 4-Methyl-pent-3-enoic acid (toluene-4-sulfonylaminocarbonyl)-amide (28490-28-0)

Tosylurethane (5577-13-9) + 5-methyl-hex-4-enoic acid amide → 1-(5-methyl-4-hexenoyl)-3-(p-tolylsulfonyl)-urea (28490-29-1)

Tosylurethane (5577-13-9) + memantine* (19982-08-2) → N'--N-<3,5-dimethyl-adamantyl-(1)>-harnstoff (100063-87-4)

Tosylurethane (5577-13-9) + 1-Adamantanamine (768-94-5) → N'-p-Toluolsulfonyl-N-adamantyl-(1)-harnstoff (17822-61-6)

Tosylurethane (5577-13-9) + N-(2-adamantyl)amine (13074-39-0) → N'--N-<3,5-dimethyl-adamantyl-(2)>-harnstoff (98654-36-5)

Tosylurethane (5577-13-9) + 3-methyl-1-aminoadamantane (78056-28-7) → N'--N-<3-methyl-adamantyl>-harnstoff (99998-84-2)

Tosylurethane (5577-13-9) + 1-amino-4-methyl-3-pentene (13296-28-1) → 1-(4-methyl-3-pentenyl)-3-(p-tolylsulfonyl)-urea (28490-23-5)

Tosylurethane (5577-13-9) + Cinnamyl bromide (4392-24-9) → ethyl cinnamyl(tosyl)carbamate (32120-97-1)

Conditions	Yield
With sodium 1.) EtOH, RT; 0.5 h, 2.) EtOH, 1 h; Multistep reaction;

Tosylurethane (5577-13-9) + prenyl bromide (870-63-3) → C15H21NO4S

Conditions	Yield
With sodium 1.) EtOH, RT; 0.5 h, 2.) EtOH, 1 h; Multistep reaction;

trans-geranyl bromide (6138-90-5) + Tosylurethane (5577-13-9) → ethyl N-geranyl-N-tosylcarbamate (124658-92-0)

Conditions	Yield
With sodium 1.) EtOH, RT; 0.5 h, 2.) EtOH, 1 h; Yield given. Multistep reaction;

Upstream product

• 541-41-3 chloroformic acid ethyl ester 
• 70-55-3 toluene-4-sulfonamide 
• 98-59-9 p-toluenesulfonyl chloride 
• 941-55-9 4-toluenesulfonyl azide 
• 64-17-5 ethanol 
• 201230-82-2 carbon monoxide 
• 31224-37-0 n-butyl tosylcarbamate 
• 14437-03-7 methyl tosylcarbamate 
• 5219-81-8 N,N'-carbonyl-bis(4-methylbenzenesulfonamide) 
• 105-58-8 Diethyl carbonate 
• 4083-64-1 Tosyl isocyanate 
• 10439-23-3 4-methylbenzenesulfinyl chloride 
• 1608-26-0 Hexamethylphosphorous triamide 
• 93506-31-1 p-Toluol-(-N-carbethoxy)-iminosulfonsaeurechlorid 

Downstream Products

• 415903-37-6 CJ-023423 
• 1330174-12-3 ethyl 2-methylene-3-oxo-1-p-tolylbutyl(tosyl)carbamate 
• 1330174-18-9 ethyl 2-methylene-3-oxo-1-phenylbutyl(tosyl)carbamate 
• 1330174-16-7 ethyl 1-(2-chlorophenyl)-2-methylene-3-oxobutyl(tosyl)carbamate 
• 1330174-15-6 ethyl 2-methylene-1-(2-nitrophenyl)-3-oxobutyl(tosyl)carbamate 
• 1330174-14-5 ethyl 2-methylene-1-(3-nitrophenyl)-3-oxobutyl(tosyl)carbamate 
• 1330174-11-2 ethyl 1-(4-chlorophenyl)-2-methylene-3-oxobutyl(tosyl)carbamate 
• 1330174-17-8 ethyl 2-methylene-1-(4-nitrophenyl)-3-oxobutyl(tosyl)carbamate 
• 1064195-49-8 N-[({1-[4-(4,9-diethoxy-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl)-3-methylbenzyl]cyclopropyl}amino)carbonyl]-4-methylbenzenesulfonamide 
• 32234-75-6 tosifen 

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