Potassium Carbonate → HCID 19066087, compound

HRID 481305Notes

Reaction equation

HRID 481305 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1.[CH2:12]([O:14][C:15](=[O:24])[CH2:16][C:17]1[S:21][C:20]([SH:22])=[N:19][C:18]=1[CH3:23])[CH3:13].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:12]([O:14][C:15](=[O:24])[CH2:16][C:17]1[S:21][C:20]([S:22][C:2]2[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=2)=[N:19][C:18]=1[CH3:23])[CH3:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 178470820HCID 178470820, compound

Product 1

HCID 19066087HCID 19066087, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
65 °C

Procedure

2-Chloro-5-trifluoromethylpyridine (Ishihara Corporation, 600 Montgomery St., San Francisco, Calif. 94111) (0.5 g, 2.8 mmol) and 5-(2-ethoxy-2-oxoethyl)-2-mercapto-4-methyl-1,3-thiazole (K. Fleishmann, K. H. Scheunemann, H. U. Schortemmer, G. Dickneite, J. Blumbad, G. F. Fischer, W. Durckheimer, and H. H. Sedlacek, Arzneim-Forsch./Drug Res., 1989, 39(II), 743) (0.6 g, 2.8 mmol) were dissolved in acetone (15 ml) under a reaction inert atmosphere. Freshly ground K2CO3 (0.42 g, 3.0 mmol) was added to this solution and the reaction was heated to 65° C. for 16 hours. The K2CO3 was filtered off and the acetone was removed via rotary evaporation. The remaining slurry was diluted with a saturated aqueous solution of sodium bicarbonate, extracted three times (200 ml) with methylene chloride, dried over MgSO4 and filtered. The solvent was then stripped off and the resulting solid was purified via flash chromatography (50% ether in hexane) to afford the title compound of this Example (0.57 g, 57% yield). 1H NMR (CDCl3): δ 8.69 (1H, d, J=2), 7.75 (1H, dd, J=8,2), 7.29 (1H, d, J=8), 4.20 (2H, q, J=7), 3.79 (2H, s), 2.43 (3H, s), 1.28 (3H, t, J=7).

Workup

  1. filtrationThe K2CO3 was filtered off
  2. customthe acetone was removed via rotary evaporation
  3. additionThe remaining slurry was diluted with a saturated aqueous solution of sodium bicarbonate
  4. extractionextracted three times (200 ml) with methylene chloride
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe resulting solid was purified via flash chromatography (50% ether in hexane)

Sources & evidence

ORD record
ord-32af1da76f094610a3a9f0b05e1bae04
Source dataset
uspto-grants-1998_08
Patent number
US05789408

Reaction notes

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