HCID 86596038, compound → 2-[4-Chloro-3-(trifluoromethyl)phenyl]-6-methyl-1,3-benzothiazole

HRID 2353365Notes

Reaction equation

HRID 2353365 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)=[S:7])=[CH:4][C:3]=1[C:18]([F:21])([F:20])[F:19]>[OH-].[Na+].CCO>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]2[S:7][C:14]3[CH:13]=[C:12]([CH3:15])[CH:11]=[CH:10][C:9]=3[N:8]=2)=[CH:4][C:3]=1[C:18]([F:21])([F:19])[F:20]

Participants

4

Reactant 1

HCID 86596038HCID 86596038, compound

Product 1

HCID 684514032-[4-Chloro-3-(trifluoromethyl)phenyl]-6-methyl-1,3-benzothiazole

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
90 °C

Procedure

To 2M aqueous solution K3Fe(CN)6 (4 mL, 8 mmol) (pre-heated to 90° C.) is added dropwise to a suspension of 4-chloro-N-p-tolyl-3-trifluoromethyl-thiobenzamide (660 mg, 2 mmol) in 2M NaOH (9 ml) and EtOH (3 ml). The mixture is heated at 90° C. overnight. The mixture is cooled to room temperature and extracted with EtOAc (50 ml×2). The combined organic layers are washed with brine, dried over MgSO4, filtered and concentrated. The mixture is purified by ISCO system (EtOAc/Hexanes: 20 minutes run 0 to 100% of EtOAc). 2-(4-Chloro-3-trifluoromethyl-phenyl)-6-methylbenzothiazole is isolated (170 mg, 26%), as well as 380 mg of the starting material.

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. extractionextracted with EtOAc (50 ml×2)
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe mixture is purified by ISCO system (EtOAc/Hexanes: 20 minutes run 0 to 100% of EtOAc)

Sources & evidence

ORD record
ord-58e157bfb01a440c9eccc041e74f5424
Source dataset
uspto-grants-2010_07
Patent number
US07750021B2

Reaction notes

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