An Efficient Method for Thiocyanation of Aromatic and Heteroaromatic Compounds using Cyanuric Chloride and Ammonium Thiocyanate under Conventional and Nonconventional Conditions

P. Venkanna; K. C. Rajanna; M. Satish Kumar; M. Venkateswarlu; M. Moazzam Ali

doi:10.1055/s-0035-1560503

Synlett, Table of Contents

Synlett 2016; 27(02): 237-240
DOI: 10.1055/s-0035-1560503

letter

An Efficient Method for Thiocyanation of Aromatic and Heteroaromatic Compounds using Cyanuric Chloride and Ammonium Thiocyanate under Conventional and Nonconventional Conditions

Authors

P. Venkanna

^aDepartment of Chemistry, Jawaharlal Nehru Technological University, Hyderabad- T. S, India
K. C. Rajanna*

^bDepartment of Chemistry, Osmania University, Hyderabad-500 007, T. S., India Email: kcrajannaou@yahoo.com
M. Satish Kumar

^bDepartment of Chemistry, Osmania University, Hyderabad-500 007, T. S., India Email: kcrajannaou@yahoo.com
M. Venkateswarlu

^bDepartment of Chemistry, Osmania University, Hyderabad-500 007, T. S., India Email: kcrajannaou@yahoo.com
M. Moazzam Ali

^cDepartment of Chemistry, Aizza College of Engineering & Technology, Hyderabad- T.S, India

Abstract

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Abstract

Highly efficient thiocyanation of aromatic and heteroaromatic compounds has been accomplished by using cyanuric chloride (NCCl)₃/NH₄SCN in dichloromethane under conventional and ultrasonic-assisted conditions. Sonicated reactions reached completion with reduced reaction times. The protocol involves a simple workup.

Key words

aromatic compounds - heteroaromatic compounds - thiocyanation - cyanuric chloride - sonication

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References

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58 Thiocyanation of Organic Compounds; Typical Procedure: Phenol (32 mmol) was added to a mixture of cyanuric chloride (32 mmol) and ammonium thiocyanate (31.6 mmol) in CH₂Cl₂ (30 mL) and the mixture was heated to reflux with stirring. The progress of the reaction was monitored by TLC (n-hexane–EtOAc, 7:3). For ultrasonically assisted reactions, the reaction mixture was ultrasonicated in a TCL (BIO-Technics India) sonicator and the progress of the reaction was followed by TLC. Upon completion of the reaction, the mixture was filtered, and the organic layer was washed with brine, dried over anhydrous Na₂SO₄, filtered, and the solvent was removed. The residue was purified by chromatography on silica (n-hexane–EtOAc) to afford 2-thiocyanatophenol. Yield: 90% (thermal) and 92% (ultrasonication). ¹H NMR (CDCl₃): δ = 7.14 (d, J = 8.1 Hz, 1 H), 6.73 (m, J = 7.9 Hz, 2 H), 6.54 (d, J = 8.1 Hz, 1 H), 4.83 (s, 1 H). MS: m/z = 151.