Ethyl tosylcarbamate

Base Information

• Chemical Name: Ethyl tosylcarbamate
• CAS No.: 5577-13-9
• Molecular Formula: C10H13NO4S
• Molecular Weight: 243.284
• Hs Code.: 2935009090
• European Community (EC) Number: 226-952-9
• DSSTox Substance ID: DTXSID80971143
• Nikkaji Number: J103.095G
• Wikidata: Q72476098
• Mol file: 5577-13-9.mol

Synonyms:Ethyl tosylcarbamate;5577-13-9;ethyl N-(4-methylphenyl)sulfonylcarbamate;Tosylurethane;Ethyl ((4-methylphenyl)sulphonyl)carbamate;ETHYL [(4-METHYLPHENYL)SULPHONYL]CARBAMATE;EINECS 226-952-9;Carbamic acid, [(4-methylphenyl)sulfonyl]-, ethyl ester;EC 226-952-9;Carbamic acid, (p-tolylsulfonyl)-, ethyl ester;Gliclazide Impurity C;Carbamic acid, ((4-methylphenyl)sulfonyl)-, ethyl ester;N-tosylurethane;Tosylcarbamic acid ethyl ester;Ethyltosylcarbamate;Ethyl p-tosylcarbamate;ETHYL-4-TOLUENESULFONYL CARBAMATE;TimTec1_005555;Oprea1_635932;Ethyl4-toluenesulfonylcarbamate;UPCMLD00WCRH1-296;SCHEMBL5931062;Ethyl (p-tolylsulfonyl)carbamate;DTXSID80971143;Ethyl (p-toluenesulfonyl)carbamate;HMS1549M11;BCP08450;Ethyl (p- Tolylsulfonyl) carbamate;Ethyl (p- Toluenesulfonyl) carbamate;MFCD00797861;AKOS016011457;NCGC00173106-01;AS-10586;Ethyl (4-methylphenyl)sulfonylcarbamate #;Ethyl[(4-methylphenyl)sulphonyl]carbamate;ethyl N-(4-methylbenzenesulfonyl)carbamate;HY-135337;CS-0111672;D70584;A830800;Ethyl hydrogen (4-methylbenzene-1-sulfonyl)carbonimidate

Chemical Property of Ethyl tosylcarbamate

Chemical Property:

• Vapor Pressure: 1.8-7.9Pa at 20-25℃
• Refractive Index: 1.53
• Boiling Point: 272℃ at 100.8-101kPa
• PSA: 80.85000
• Density: 1.261 g/cm³
• LogP: 2.90150
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 243.05652907
• Heavy Atom Count: 16
• Complexity: 325

Purity/Quality:

99.9% ^*data from raw suppliers

Tosylurethane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)NS(=O)(=O)C1=CC=C(C=C1)C
• Uses: Tosylurethane (Gliclazide EP Impurity C) is an intermediate in the synthesis of Gliclazide (G409877), a sulfonylurea hypoglycemic agent. Used as an antidiabetic.

Technology Process of Ethyl tosylcarbamate

There total 12 articles about Ethyl tosylcarbamate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

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

Guidance literature:

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

DOI:10.1002/anie.201600887

Reference yield: 94.0%

→ Tosylurethane (5577-13-9)

Guidance literature:

With palladium diacetate; In acetonitrile; at 20 ℃; for 12h; under 20 Torr;

Reference yield: 90.0%

N,N'-carbonyl-bis(4-methylbenzenesulfonamide) (5219-81-8) + Diethyl carbonate (105-58-8,76619-83-5) → Tosylurethane (5577-13-9)

Guidance literature:

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

DOI:10.1080/00397911003707055

upstream raw materials:

chloroformic acid ethyl ester

toluene-4-sulfonamide

p-Toluol-(-N-carbethoxy)-iminosulfonsaeurechlorid

Hexamethylphosphorous triamide

Downstream raw materials:

N-(2-methoxy-ethyl)-N'-(toluene-4-sulfonyl)-urea

tosifen

ethyl 2-methylene-1-(4-nitrophenyl)-3-oxobutyl(tosyl)carbamate

ethyl 1-(4-chlorophenyl)-2-methylene-3-oxobutyl(tosyl)carbamate

Refernces

• 1、 Xi, Pin-Xian,Xu, Zhi-Hong,Liu, Xiao-Hui,Chen, Feng-Juan,Huang, Liang,Zeng, Zheng-Zhi. "Synthesis, characterization, antioxidant activity, and DNA-binding studies of 1-cyclohexyl-3-tosylurea and its Nd(III), Eu(III) complexes". . p. 541 - 546. Retrieved 2008.
• 2、 -. "A sulfonyl urea, sulfonamide ethyl ester preparation method of compound (by machine translation)". Paragraph 0094; 0100-0104; 0110-0115. . Retrieved 2017/08/02.
• 3、 Zhao, Jin,Li, Zongyang,Song, Shaole,Wang, Ming-An,Fu, Bin,Zhang, Zhenhua. "Product-Derived Bimetallic Palladium Complex Catalyzes Direct Carbonylation of Sulfonylazides". supporting information. p. 5545 - 5549. Retrieved 2016/05/09.