Hydrochloric Acid → 5-(trifluoromethyl)-1,3-benzothiazole-2-thiol

HRID 1507517Notes

Reaction equation

HRID 1507517 reaction equation
Br[C:2]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:3]=1[NH2:4].C(O[C:16]([S:18][K])=[S:17])C.O.Cl>CN(C)C=O>[F:10][C:9]([F:12])([F:11])[C:6]1[CH:7]=[CH:8][C:2]2[S:17][C:16]([SH:18])=[N:4][C:3]=2[CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 679892-Bromo-5-(trifluoromethyl)benzenamineHCID 178473699HCID 178473699, compound

Product 1

HCID 1784190875-(trifluoromethyl)-1,3-benzothiazole-2-thiol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Into a solution of 2-bromo-5-(trifluoromethyl)aniline (1.5 g, 6.25 mmol, 1.00 equiv) in N,N-dimethylformamide (10.0 mL) was added ethoxy(potassiosulfanyl)methanethione (2.2 g, 13.72 mmol, 2.20 equiv) under nitrogen. The resulting mixture was heated for 4 h at 120° C. in an oil bath. After cooled down, water (70.0 mL) and hydrogen chloride (15.0 mL, 1 mol/L) were added. The solid was collected by filtration, dissolved in ethyl acetate and dried over anhydrous sodium sulfate. Filtration and evaporation of the solvent afforded the title compound. as a gray white solid. MS m/z [M+H]+ (ESI): 236

Workup

  1. temperatureAfter cooled down
  2. filtrationThe solid was collected by filtration
  3. dissolutiondissolved in ethyl acetate
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationFiltration and evaporation of the solvent

Sources & evidence

ORD record
ord-c9316add5cf2480ab7f6cab0eea225d4
Source dataset
uspto-grants-2015_12
Patent number
US09221809B2

Reaction notes

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