672 JOURNAL OF CHEMICAL RESEARCH 2016
MHz, DMSO-d6) δ 182.5, 151.9, 142.2, 134.6, 126.6, 125.8, 125.2,
110.5, 107.2, 42.2, 40.5; HRMS (ESI) calcd for C11H13N2OS2+ [M + H]+:
253.0464; found: 253.0470.
yields as well as using water as solvent are the major advantages
of the method.
Experimental
Acknowledgements
All of the chemicals and reagents were obtained from established
suppliers (Sigma-Aldrich or Aladdin) and used as received. NMR
spectra were obtained on a Bruker 300 or 400 MHz spectrometer in
CDCl3 or in DMSO-d6 using TMS as an internal standard. Chemical
shifts (δ) are given in ppm and coupling constants (J) are given in Hz.
Melting points (m.p.) were determined with a MPA 100 apparatus
without correction. LCMS was performed on a Shimadzu LCMS-2020
instrument with an ESI source. HRMS was performed on an Agilent
6540 Q-TOF MS instrument with an ESI source.
We gratefully acknowledge the National Natural Science
Foundation of China (Nos. 21002009 and 21572026), the
Scientific and Technological Project of Jiangsu Province
(BY2014037-01), the Natural Science Foundation of Jiangsu
Colleges and Universities (14KJA150002), Changzhou
University, Advanced Catalysis and Green Manufacturing
Collaborative Innovation Center, and the Priority Academic
Program Development of Jiangsu Higher Education Institutions.
Synthesis of thiocarbamates (3); general procedure
Electronic Supplementary Information
Phenyl chlorothionoformate (345 mg, 2.0 mmol), amine 2 (4.0 mmol)
and water (15 mL) were added successively to a 50 mL round-bottom
flask. The reaction mixture was stirred at room temperature for 1 h
(monitored by TLC). After the reaction was complete, the solid was
filtered off, washed with 10% HCl (2 × 20 mL) and deionised water
(2 × 20 mL), and dried under vacuum to give the pure thiocarbamates
3. All products are known compounds and were identified by
comparison of their physical and spectral data with those reported in
the literature.28
The ESI (full characterization and1H and 13C NMR spectra of
4a–4y) is available through:
stl.publisher.ingentaconnect.com/content/stl/jcr/supp-data
Received 7 August 2016; accepted 9 September 2016
Published online: 21 October 2016
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