18-Crown-6 → HCID 18374284, compound

HRID 2300027Notes

Reaction equation

HRID 2300027 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([O:10]C)=[O:9])=[C:4]([C:12]([F:15])([F:14])[F:13])[CH:3]=1.C1OCCOCCOCCOCCOCCOC1.[CH3:34][S-:35]>CC(C)=O>[CH3:34][S:35][C:2]1[CH:3]=[C:4]([C:12]([F:15])([F:14])[F:13])[C:5]([C:8]([OH:10])=[O:9])=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 519392MercaptomethanideHCID 2775340Methyl 6-chloro-4-(trifluoromethyl)nicotinate

Product 1

HCID 18374284HCID 18374284, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In boiling acetone, 0.70 g (2.9 mol) of methyl 6-chloro-4-trifluoromethylpyridin-3-ylcarboxylate is treated in the presence of a catalytic amount of 18-crown-6 with methanethiolate (0.33 g) until no further conversion can be detected by gas chromatographic analysis. The mixture is then filtered through silica gel and evaporated. This gives 0.73 g of methyl 6-methylthio-4-trifluoromethylpyridin-3-yicarboxylate; 1H NMR (CDCl3, ppm): 8.98, s, 1H; 7.48, S, 1H; 3.94, s, 3H; 2.64, s, 3H. Hydrolysis under the conditions mentioned above gives 6-methylthio-4-trifluoromethylnicotinic acid: 1H NMR (CDCl3, ppm): 9.02, s, 1H; 7.46, s, 1H; 2.64, s, 3H.

Workup

  1. filtrationThe mixture is then filtered through silica gel
  2. customevaporated
  3. customHydrolysis under the conditions

Sources & evidence

ORD record
ord-fcead73561b64813832faeb99f40c200
Source dataset
uspto-grants-2002_12
Patent number
US06498125B2

Reaction notes

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