Sodium methanethiolate → 2-(4-Chloro-3-methoxyphenyl)-5-trifluoromethyl-3-methylthiopyridine

HRID 1957247Notes

Reaction equation

HRID 1957247 reaction equation
Cl[C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([O:19][CH3:20])[CH:13]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[CH3:21][S-:22].[Na+]>CO.CN(C)C=O>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([C:3]2[C:2]([S:22][CH3:21])=[CH:7][C:6]([C:8]([F:11])([F:10])[F:9])=[CH:5][N:4]=2)=[CH:13][C:14]=1[O:19][CH3:20]

Participants

5

Reactant 2

HCID 4378561Sodium methanethiolateHCID 157668763-Chloro-2-(4-chloro-3-methoxyphenyl)-5-trifluoromethylpyridine

Product 1

HCID 190687562-(4-Chloro-3-methoxyphenyl)-5-trifluoromethyl-3-methylthiopyridine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

3.0 g (9.3 mmol) of 3-chloro-2-(4-chloro-3-methoxyphenyl)-5-trifluoromethylpyridine and 0.7 g (10 mmol) of sodium thiomethoxide in a mixture of 50 ml of methanol and 20 ml of dimethylformamide were stirred at 80° C. for 7 h and then at 23° C. for 72 h. The mixture was then poured into 500 ml of ice-water, which was then extracted three times with 150 ml of tert-butyl methyl ether each time. The combined organic phases were washed twice with 100 ml of water each time, dried over sodium sulfate and concentrated.

Workup

  1. waitat 23° C. for 72 h
  2. extractionwas then extracted three times with 150 ml of tert-butyl methyl ether each time
  3. washThe combined organic phases were washed twice with 100 ml of water each time
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-733dc18d305e4a5abf469d33ba1e9ad2
Source dataset
uspto-grants-1998_07
Patent number
US05783522

Reaction notes

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