Carbon Disulfide → CID 616624

Reaction equation

[H-].[Na+].C(OCCOCCO)C.Cl[C:13]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:14]=1[NH2:15].[C:24](=[S:26])=[S:25]>>[SH:26][C:24]1[S:25][C:13]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:14]=2[N:15]=1

Participants

Reactant 4

HCID 6348Carbon Disulfide

HCID 8146Diethylene Glycol Monoethyl Ether

HCID 8475Benzenamine, 2-chloro-5-(trifluoromethyl)-

HCID 24758Sodium hydride

Product 1

HCID 178419087CID 616624Yield 44.1%

Procedure

To a mixture of sodium hydride (0.98 g, 40.91 mmol) and diethylene glycol monoethyl ether (25 mL) was added 2-chloro-5-(trifluoromethyl)aniline (5.00 g, 25.57 mmol) under a nitrogen atmosphere. The resulting mixture was stirred at rt for 30 minutes, and then carbon disulfide (3.89 g, 51.13 mmol) was added. The reaction mixture was then heated at 140° C. for 6 hours. After cooling the solution to rt, the product was precipitated by addition of conc. HCl, collected by filtration, and recrystallized from isopropyl ether to afford 2-mercapto-5-(trifluoromethyl)benzothiazole (2.65 g, 44%). 1H NMR (400 MHz, DMSO-d6) δ 7.49 (s, 1H), 7.61 (d, 1H), 7.94 (d, 1H).