3-BIPHENYL ISOTHIOCYANATE

To a stirred solution of biphenyl-3-ylamine (338 mg, 2 mmol) in DCM (5 mL), thiocarbonyldiimidazole (TCDI) (535 mg, 3 mmol) and DMAP (48.8 mg, 0.04 mmol) were added and the reaction mixture stirred at r.t under NGeneral procedure: To a stirred solution of General procedure: 3-Isothiocyanato-1, 1'-biphenyl (1 equiv.) was added to 5 mL of CH3CN, followed by the appropriate cycloalkanamine (1 equiv.) and DMAP (0.2 equiv.). The reaction mixture was left to stir at room temperature for 2 h. After this time the solvent was removed in vacuo to leave a white solid and purified by a silica plug (4:1 hexane/EtOAc). The major product fractions were evaporated to dryness and the residual solid recrystallised (DCM/hexane). The following compounds were prepared in this manner.General procedure: 3-Isothiocyanato-1, 1'-biphenyl (1 equiv.) was added to 5 mL of CH3CN, followed by the appropriate cycloalkanamine (1 equiv.) and DMAP (0.2 equiv.). The reaction mixture was left to stir at room temperature for 2 h. After this time the solvent was removed in vacuo to leave a white solid and purified by a silica plug (4:1 hexane/EtOAc). The major product fractions were evaporated to dryness and the residual solid recrystallised (DCM/hexane). The following compounds were prepared in this manner.TCDI (567 mg, 3.19 mmol) and DMAP (39mg, 0.32 mmol) were added to a stirred solution of biphenyl-3-ylamine (360 mg, 2.13 mmol) in DCM (5 mL). The reaction was stirred at r.t under N2 for 1 h. Following this, methanolic ammonia (4.3 mL) was added and the reaction continued for a further 2 h until a solid began to form. The DCM was then removed in vacuo to leave an orange solid. The product was purified via a silica plug (49:1 CHCl3/MeOH) and recrystallised to give small sharp light yellow crystals (478 mg, 98%). Rf: 0.38 (49:1 CHCl3/MeOH). mp: 178.4-180 C (DCM/hexane). 1H NMR (d6-acetone): delta 7.06 (s, 2H, H3), 7.45 (tt, 1H, J 4, 1.3 Hz, H4''), 7.47-7.50 (m, 5H, H4', H6', H3'', H5'', H5'), 7.67 (m, 2H, H2'', H6''), 7.82 (s, 1H, H2'), 9.16 (s, 1H, H1). 13C NMR (d6-acetone): delta 123.1 (CH), 123.4 (CH), 124.6 (CH), 127.8 (CH), 128.5 (CH), 129.8 (CH), 130.4 (CH), 140.4 (C), 141.2 (C), 142.7 (C), 183.5 (CS). LRMS (ESI) m/z: [M-H]- 227.3 (53%), [M+H]+ 229.3 (100%).

Molecular Weight:211.28
XLogP3:5.4
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:211.04557046
Monoisotopic Mass:211.04557046
Topological Polar Surface Area:44.4
Heavy Atom Count:15
Complexity:239
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes