Hydrochloric Acid → 2-Chloro-6-trifluoromethylbenzothiazole

HRID 2427355Notes

Reaction equation

Cl[C:2]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[C:13](=[S:18])(OCC)[S-].[K+].[ClH:20]>CN(C=O)C>[Cl:20][C:13]1[S:18][C:2]2[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:3]=2[N:4]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 2-chloro-4-trifluoromethylaniline (15.0 g, 76.7 mmol) and potassium O-ethyl dithiocarbonate (29.5 g, 184.1 mmol) in 75 mL anhydrous DMF was heated at 130° C. overnight under a nitrogen atmosphere. The reaction mixture was cooled to rt, and then 1 N HCl solution (200 mL) was added with stirring to induce precipitation. After the mixture was stirred for 30 minutes, the solid precipitate was collected by filtration and rinsed with water. The filter cake was dissolved in 100 mL EtOAc, and the solution was dried over Na2SO4. EtOAc was removed by rotary evaporation, and the residue was dried in vacuo to afford the desired product as a white solid (18.0 g, 99%). 1H NMR (DMSO-d6) δ 14.00 (bs, 1 H), 8.20 (s, 1 H), 7.70 (d, 1 H), 7.40 (d, 1 H); GC-EIMS m/z 235 (M+).

Workup

temperatureThe reaction mixture was cooled to rt
customprecipitation
stirringAfter the mixture was stirred for 30 minutes
filtrationthe solid precipitate was collected by filtration
washrinsed with water
dissolutionThe filter cake was dissolved in 100 mL EtOAc
dry with materialthe solution was dried over Na2SO4
customEtOAc was removed by rotary evaporation
customthe residue was dried in vacuo

Sources & evidence

ORD record: ord-5b677918abe9461c9c5df4fd50a982b9
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968576B2

Reaction notes

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