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Synlett 2016; 27(02): 237-240
DOI: 10.1055/s-0035-1560503
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
Further Information
Publication History
Received: 07 August 2015
Accepted after revison: 15 September 2015
Publication Date:
20 October 2015 (online)
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.
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References and Notes
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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.