Potassium Carbonate → HCID 58797754, compound

HRID 446189Notes

Reaction equation

HRID 446189 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+].[Br:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27]Br)[CH:22]=1>CC(C)=O>[C:1]([C:3]1[S:4][C:5]2[CH:11]=[C:10]([O:12][CH2:27][C:23]3[CH:24]=[CH:25][CH:26]=[C:21]([CH2:20][Br:19])[CH:22]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1)#[N:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 69373Benzene, 1,3-bis(bromomethyl)-HCID 98819122-Cyano-6-hydroxybenzothiazole

Product 1

HCID 58797754HCID 58797754, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-cyano-6-hydroxybenzothiazole (1.04 g) in 30 mL of acetone was added potassium carbonate (1.63 g), followed by α,α′-dibromo-m-xylene (4.7 g). The resultant solution was stirred at RT for 1 hour and the solvent was removed under reduced pressure. The residue was resuspended in dichloromethane and washed with water. The aqueous phase was extracted with more dichloromethane (2×) and the organic extracts were combined, dried over sodium sulfate, and purified by flash chromatography using dichloromethane. 1.945 g of product was obtained.

Workup

  1. customthe solvent was removed under reduced pressure
  2. washwashed with water
  3. extractionThe aqueous phase was extracted with more dichloromethane (2×)
  4. dry with materialdried over sodium sulfate
  5. custompurified by flash chromatography

Sources & evidence

ORD record
ord-567c599e409e44d6bb01ba06ea6177a8
Source dataset
uspto-grants-2013_07
Patent number
US08476450B2

Reaction notes

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