Potassium Carbonate → 6-Ethynyl-1,3-benzothiazole

HRID 2244115Notes

Reaction equation

HRID 2244115 reaction equation
C(=O)([O-])[O-].[K+].[K+].C[Si]([C:11]#[C:12][C:13]1[CH:21]=[CH:20][C:16]2[N:17]=[CH:18][S:19][C:15]=2[CH:14]=1)(C)C>CO>[C:12]([C:13]1[CH:21]=[CH:20][C:16]2[N:17]=[CH:18][S:19][C:15]=2[CH:14]=1)#[CH:11]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 231545826-Trimethylsilanylethynylbenzothiazol

Product 1

HCID 231545886-Ethynyl-1,3-benzothiazoleYield 96.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (29.7 g) was added to a solution of 6-trimethylsilanylethynylbenzothiazol (45.1 g) in methanol (600 ml), and the mixture was stirred for 1.5 hours at room temperature. The reaction solution was filtered, and then the resultant was washed with methanol and ethyl acetate successively. The filtrate was concentrated, to which water was added, and then extracted with ethyl acetate. The organic layer, which was washed with a brine, was dried over anhydrous magnesium sulfate. After the solvent was evaporated, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→1:1) to yield 6-ethynylbenzothiazole (30.0 g) as a light yellow solid (mp: 47.5-49.0° C.).

Workup

  1. filtrationThe reaction solution was filtered
  2. washthe resultant was washed with methanol and ethyl acetate successively
  3. concentrationThe filtrate was concentrated, to which water
  4. additionwas added
  5. extractionextracted with ethyl acetate
  6. washThe organic layer, which was washed with a brine
  7. dry with materialwas dried over anhydrous magnesium sulfate
  8. customAfter the solvent was evaporated
  9. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→1:1)

Sources & evidence

ORD record
ord-0079baf0a95844538dcdefce8e31c9cd
Source dataset
uspto-grants-2010_03
Patent number
US07678810B2

Reaction notes

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