Carbon Disulfide → 5-(trifluoromethyl)-1,3-benzothiazole-2-thiol

HRID 2240329Notes

Reaction equation

HRID 2240329 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[SH:13].[C:14](=S)=[S:15].[OH-].[K+]>CCO>[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[CH:5][C:4]2[S:13][C:14]([SH:15])=[N:2][C:3]=2[CH:8]=1

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 27346782-Amino-4-(trifluoromethyl)benzenethiol hydrochloride

Product 1

HCID 1784190875-(trifluoromethyl)-1,3-benzothiazole-2-thiolYield 72.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into a 25 ml round bottomed flask were added 2-amino-4-(trifluoromethyl)benzenethiol hydrochloride (107 mg, 0.43 mmol), CS2 (331 mg, 4.35 mmol), aqueous KOH (127 mg, 2.3 mmol), and EtOH (5 ml). The solution was refluxed under Ar for 2 h, cooled to rt, then treated with Amberlite IR-120(H+) (2 g, 3.8 mmol). The solution was filtered and concentrated to afford the title compound as a white crystalline solid (73.4 mg, 67%). 1H NMR (DMSO-d6) δ=7.46 (s, 1H), 7.61 (d, 1H), 7.93 (d, 1H), 13.99 (br s, 1H); ESIMS: m/z 234 (M−H).

Workup

  1. temperatureThe solution was refluxed under Ar for 2 h
  2. filtrationThe solution was filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-8eadc7bd8e494c1e9cae0742f536b344
Source dataset
uspto-grants-2010_05
Patent number
US07723366B2

Reaction notes

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