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New facile one-pot synthesis of S-alkyl thiolcarbamates from xanthogenate in water

Authorized Users Only
2013
Authors
Milosavljević, Milutin M.
Mijin, Dušan
Milisavljević, Smiljka S.
Elezović, Nataša M.
Milanović, Jelena K.
Article (Published version)
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Abstract
A simple and efficient one-pot synthesis was developed for the preparation of S-alkyl thiolcarbamates from xanthogenate without catalyst using water as a solvent. The water can be recycled after removal of the product. The significant features of this protocol are: operational simplicity, mild reaction conditions, recycling of solvent and high product yields. Starting basic alkyl xanthogenate reacts with alkyl ammonium sulfate (aryl ammonium sulfate) and hydrogen peroxide (molar ratio 1:0.55:1) in water at 40 A degrees C for 1 h, followed by additional heating at 70-110 A degrees C for 1-2.3 h. Good to excellent yields were achieved using ammonium sulfate in 10 % molar excess.
Keywords:
Amines / Catalyst-free reaction / Fungicides / Alkyl ammonium sulfate / Aryl ammonium sulfate
Source:
Monatshefte Fur Chemie, 2013, 144, 12, 1833-1837
Publisher:
  • Springer Wien, Wien
Funding / projects:
  • Study of the Synthesis, Structure and Activity of Natural and Synthetic Organic Compounds (RS-172013)

DOI: 10.1007/s00706-013-1083-7

ISSN: 0026-9247

WoS: 000327083100011

Scopus: 2-s2.0-84890099477
[ Google Scholar ]
3
3
URI
http://TechnoRep.tmf.bg.ac.rs/handle/123456789/2442
Collections
  • Radovi istraživača / Researchers’ publications (TMF)
Institution/Community
Tehnološko-metalurški fakultet
TY  - JOUR
AU  - Milosavljević, Milutin M.
AU  - Mijin, Dušan
AU  - Milisavljević, Smiljka S.
AU  - Elezović, Nataša M.
AU  - Milanović, Jelena K.
PY  - 2013
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/2442
AB  - A simple and efficient one-pot synthesis was developed for the preparation of S-alkyl thiolcarbamates from xanthogenate without catalyst using water as a solvent. The water can be recycled after removal of the product. The significant features of this protocol are: operational simplicity, mild reaction conditions, recycling of solvent and high product yields. Starting basic alkyl xanthogenate reacts with alkyl ammonium sulfate (aryl ammonium sulfate) and hydrogen peroxide (molar ratio 1:0.55:1) in water at 40 A degrees C for 1 h, followed by additional heating at 70-110 A degrees C for 1-2.3 h. Good to excellent yields were achieved using ammonium sulfate in 10 % molar excess.
PB  - Springer Wien, Wien
T2  - Monatshefte Fur Chemie
T1  - New facile one-pot synthesis of S-alkyl thiolcarbamates from xanthogenate in water
EP  - 1837
IS  - 12
SP  - 1833
VL  - 144
DO  - 10.1007/s00706-013-1083-7
ER  - 
@article{
author = "Milosavljević, Milutin M. and Mijin, Dušan and Milisavljević, Smiljka S. and Elezović, Nataša M. and Milanović, Jelena K.",
year = "2013",
abstract = "A simple and efficient one-pot synthesis was developed for the preparation of S-alkyl thiolcarbamates from xanthogenate without catalyst using water as a solvent. The water can be recycled after removal of the product. The significant features of this protocol are: operational simplicity, mild reaction conditions, recycling of solvent and high product yields. Starting basic alkyl xanthogenate reacts with alkyl ammonium sulfate (aryl ammonium sulfate) and hydrogen peroxide (molar ratio 1:0.55:1) in water at 40 A degrees C for 1 h, followed by additional heating at 70-110 A degrees C for 1-2.3 h. Good to excellent yields were achieved using ammonium sulfate in 10 % molar excess.",
publisher = "Springer Wien, Wien",
journal = "Monatshefte Fur Chemie",
title = "New facile one-pot synthesis of S-alkyl thiolcarbamates from xanthogenate in water",
pages = "1837-1833",
number = "12",
volume = "144",
doi = "10.1007/s00706-013-1083-7"
}
Milosavljević, M. M., Mijin, D., Milisavljević, S. S., Elezović, N. M.,& Milanović, J. K.. (2013). New facile one-pot synthesis of S-alkyl thiolcarbamates from xanthogenate in water. in Monatshefte Fur Chemie
Springer Wien, Wien., 144(12), 1833-1837.
https://doi.org/10.1007/s00706-013-1083-7
Milosavljević MM, Mijin D, Milisavljević SS, Elezović NM, Milanović JK. New facile one-pot synthesis of S-alkyl thiolcarbamates from xanthogenate in water. in Monatshefte Fur Chemie. 2013;144(12):1833-1837.
doi:10.1007/s00706-013-1083-7 .
Milosavljević, Milutin M., Mijin, Dušan, Milisavljević, Smiljka S., Elezović, Nataša M., Milanović, Jelena K., "New facile one-pot synthesis of S-alkyl thiolcarbamates from xanthogenate in water" in Monatshefte Fur Chemie, 144, no. 12 (2013):1833-1837,
https://doi.org/10.1007/s00706-013-1083-7 . .

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