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

HRID 1865512Notes

Reaction equation

HRID 1865512 reaction equation
C(O[C:4]([SH:6])=[S:5])C.[K].Br[C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:10]=1[NH2:19].Cl>CN(C)C=O>[SH:6][C:4]1[S:5][C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:16])([F:18])[F:17])=[CH:11][C:10]=2[N:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8823Ethyl xanthateHCID 679892-Bromo-5-(trifluoromethyl)benzenamineHCID 5462222Potassium

Product 1

HCID 1784190875-(trifluoromethyl)-1,3-benzothiazole-2-thiolYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In analogy to the procedure of Chaudhuri, N. Synth. Commun. 1996, 26, 20, 3783, O-ethylxanthic acid, potassium salt (Lancaster, 7.5 g, 46.9 mmol) was added to a solution of 2-bromo-5-trifluoromethylphenylamine (Aldrich, 5.0 g, 20.8 mmol) in N,N-dimethylformamide (DMF, 30 mL). The mixture was heated to reflux for 4 hours. After cooling to room temperature, the mixture was poured into ice water and acidified with 2N HCl. The solid product was collected by filtration. Recrystallization from CHCl3/Hexanes gave 239 (4.5 g, 92%) as a white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 hours
  3. filtrationThe solid product was collected by filtration
  4. customRecrystallization from CHCl3/Hexanes

Sources & evidence

ORD record
ord-8f545055303140f893eae392d9c3a788
Source dataset
uspto-grants-2009_12
Patent number
US07626033B2

Reaction notes

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