Basic information Safety Supplier Related

Ethyl N-(4-methylphenyl)sulfonylcarbamate

Basic information Safety Supplier Related

Ethyl N-(4-methylphenyl)sulfonylcarbamate 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
  • 3-ethyl-4-methylbenzenesulfonic acid carbamoyl ester
  • ethyl tosylcarbaMate
  • Gliclazide IMpurity C
CAS:
5577-13-9
MF:
C10H13NO4S
MW:
243.28
EINECS:
226-952-9
Mol File:
5577-13-9.mol
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Ethyl N-(4-methylphenyl)sulfonylcarbamate Chemical Properties

Melting point:
82-84oC
Boiling point:
272℃ at 100.8-101kPa
Density 
1.38 at 20℃
vapor pressure 
1.8-7.9Pa at 20-25℃
storage temp. 
Sealed in dry,Room Temperature
solubility 
Chloroform (Slightly), Ethyl Acetate (Slightly)
form 
Solid
color 
White
LogP
0.73-1.7 at 23℃ and pH2-7
Surface tension
63.8mN/m at 1g/L and 20℃
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Ethyl N-(4-methylphenyl)sulfonylcarbamate Usage And Synthesis

Uses

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

Synthesis

64-17-5

31224-37-0

5577-13-9

GENERAL STEPS: Dissolve 4-methylphenylsulfonylcarbamate (Compound, CAS:31224-37-0) in selected alcohol (ethanol, 2 mL) in a microwaveable reaction vial. The reaction vial was sealed using an aluminum cap with a PTFE-faced septum. The reaction mixture was placed in a microwave reactor and radiantly heated at 100-120°C for 20-60 min. Upon completion of the reaction, the crude product was concentrated under reduced pressure and the residue was subsequently purified by silica gel column chromatography to finally obtain the target product, ethyl N-(4-methylphenyl)sulfonylcarbamate.

References

[1] Tetrahedron Letters, 2016, vol. 57, # 13, p. 1476 - 1478

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