Potassium Carbonate → 2-Cyano-6-(2-trifluoromethylbenzyloxy)benzothiazole

HRID 446191Notes

Reaction equation

HRID 446191 reaction equation
[C:1]([C:3]1[S:4][C:5]2[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:6]=2[N:7]=1)#[N:2].C(=O)([O-])[O-].[K+].[K+].[F:19][C:20]([F:30])([F:29])[C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH2:23]Br>CC(C)=O>[C:1]([C:3]1[S:4][C:5]2[CH:11]=[C:10]([O:12][CH2:23][C:22]3[CH:25]=[CH:26][CH:27]=[CH:28][C:21]=3[C:20]([F:19])([F:29])[F:30])[CH:9]=[CH:8][C:6]=2[N:7]=1)#[N:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1230571-(Bromomethyl)-2-(trifluoromethyl)benzeneHCID 98819122-Cyano-6-hydroxybenzothiazole

Product 1

HCID 587977072-Cyano-6-(2-trifluoromethylbenzyloxy)benzothiazoleYield 77.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-cyano-6-hydroxybenzothiazole (100 mg, 0.568 mmol) in 10 mL of acetone was added potassium carbonate (157 mg, 1.14 mmol), followed by 2-(trifluoromethyl)benzyl bromide (204 mg, 0.852 mmol). The mixture was then stirred at RT for about 5 hrs. The solvent was then removed under reduced pressure and the residue was dissolved in dichloromethane. The resultant solution was then extracted with dichloromethane. The organic phase was dried over sodium sulfate and purified by flash chromatography using dichloromethane. 148 mg of product was obtained.

Workup

  1. customThe solvent was then removed under reduced pressure
  2. dissolutionthe residue was dissolved in dichloromethane
  3. extractionThe resultant solution was then extracted with dichloromethane
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. custompurified by flash chromatography

Sources & evidence

ORD record
ord-68eb7c4cda194a0eaa296cd39fd7d3df
Source dataset
uspto-grants-2013_07
Patent number
US08476450B2

Reaction notes

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