Hydrochloric Acid → HCID 70663362, compound

HRID 878214Notes

Reaction equation

HRID 878214 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[N:10]=1)[C:5]([OH:7])=[O:6].[CH3:15][S-:16].[Na+].CCOC(C)=O.Cl>C1COCC1>[CH3:15][S:16][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[N:10]=1)[C:5]([OH:7])=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 4378561Sodium methanethiolateHCID 112183892-Chloro-6-(trifluoromethyl)pyridine-4-carboxylic acid

Product 1

HCID 70663362HCID 70663362, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of 2-chloro-6-(trifluoromethyl)isonicotinic acid (0.1 g, 443 μmol, prepared according to F. Cottet, M. Schlosser, Eur. J. Org. Chem. 2004, 18, 3793-3798) in THF (5 mL) was added sodium thiomethoxide (155 mg, 2.22 mmol, CAS RN 50615-16-2) and the reaction mixture was heated to 70° C. (oil bath temperature) for 15 hours. After cooling down to room temperature, EtOAc (5 mL) and 1M aqueous HCl (2 mL) were added and the reaction mixture was stirred at room temperature for 30 min. The layers were separated and the aqueous layer was extracted with EtOAc. The organic layers were washed with brine, dried over MgSO4, filtered and evaporated to give the desired compound as an off-white solid (0.105 g; 99%) which was used in the next step without further purification. MS (ESI): m/z=236.01 [M−H]−.

Workup

  1. temperatureAfter cooling down to room temperature
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc
  4. washThe organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-bc5e6b84f4ff4eb2b25a37d4c578c786
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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