Water → 3-(2,3,4-Trimethoxy-6-methylbenzoyl)-2-methylthio-4-trifluoromethylpyridine

HRID 1835412Notes

Reaction equation

HRID 1835412 reaction equation
[CH3:1][S-:2].[Na+].CN(C)C=O.[CH3:9][O:10][C:11]1[C:29]([O:30][CH3:31])=[C:28]([O:32][CH3:33])[CH:27]=[C:26]([CH3:34])[C:12]=1[C:13]([C:15]1[C:16](Cl)=[N:17][CH:18]=[CH:19][C:20]=1[C:21]([F:24])([F:23])[F:22])=[O:14].O>C(OCC)(=O)C>[CH3:9][O:10][C:11]1[C:29]([O:30][CH3:31])=[C:28]([O:32][CH3:33])[CH:27]=[C:26]([CH3:34])[C:12]=1[C:13]([C:15]1[C:16]([S:2][CH3:1])=[N:17][CH:18]=[CH:19][C:20]=1[C:21]([F:24])([F:23])[F:22])=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 4378561Sodium methanethiolateHCID 121515333-(2,3,4-Trimethoxy-6-methylbenzoyl)-2-chloro-4-trifluoromethylpyridine

Product 1

HCID 121515423-(2,3,4-Trimethoxy-6-methylbenzoyl)-2-methylthio-4-trifluoromethylpyridineYield 58.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Sodium methanethiolate (0.32 g) was added to a dimethylformamide (15 ml) solution of 0.9 g of 3-(2,3,4-trimethoxy-6-methylbenzoyl)-2-chloro-4-trifluoromethylpyridine (compound No. 11) at room temperature, followed by stirring for 1 hour. The mixture was poured into water (50 ml), and extraction with ethyl acetate was carried out. The ethyl acetate phase was dried over sodium sulfate, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 0.54 g (yield 58%) of 3-(2,3,4-trimethoxy-6-methylbenzoyl)-2-methylthio-4-trifluoromethylpyridine (compound No. 50; pale yellow oily substance), and its structure was confirmed by nuclear magnetic resonance spectrum.

Workup

  1. customat room temperature
  2. dry with materialThe ethyl acetate phase was dried over sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-cdee8d535ef3414f8a70a9c534dbc349
Source dataset
uspto-grants-2004_08
Patent number
US06770662B2

Reaction notes

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