Potassium Carbonate → HCID 66702981, compound

HRID 424450Notes

Reaction equation

HRID 424450 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][C:24]([CH2:25]Br)=[CH:23][CH:22]=1>CC(C)=O>[F:19][C:20]([F:29])([F:30])[C:21]1[CH:28]=[CH:27][C:24]([CH2:25][O:12][C:10]2[CH:9]=[CH:8][C:6]3[N:7]=[C:3]([C:1]#[N:2])[S:4][C:5]=3[CH:11]=2)=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 98819122-Cyano-6-hydroxybenzothiazole

Product 1

HCID 66702981HCID 66702981, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 2-cyano-6-hydroxybenzothiazole (1.0 g, 5.68 mmol) in acetone (5 mL) was prepared in a 100-mL 2-necked round-bottomed flask fitted with a reflux condenser. Anhydrous potassium carbonate (0.94 g, 6.82 mmol) was added to the reaction mixture and the suspension turned to a yellow solution. Then 4-(trifluoromethyl)benzyl bromide (1.49 g, 6.25 mmol) was added and the reaction mixture was heated at reflux for 15 h using a heated stir plate and oil bath. The reaction mixture was allowed to cool to ambient temperature and then filtered to remove inorganic salts. The filtrate was concentrated by rotoevaporation to provide 1.7 g (89% yield) of an off-white solid that was used without purification. The structure was confirmed by 1H NMR analysis in DMSO-d6.

Workup

  1. customwas prepared in a 100-mL 2-necked round-bottomed flask
  2. customfitted with a reflux condenser
  3. temperaturethe reaction mixture was heated
  4. temperatureat reflux for 15 h
  5. filtrationfiltered
  6. customto remove inorganic salts
  7. concentrationThe filtrate was concentrated by rotoevaporation

Sources & evidence

ORD record
ord-5bc62e27682a443f95dcb1f51643ca1c
Source dataset
uspto-grants-2012_01
Patent number
US08106052B2

Reaction notes

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