Water → 6-(2,6-Diethyl-phenyl)-2-methyl-4-methylsulfanyl-nicotinic acid ethyl ester

HRID 1392666Notes

Reaction equation

HRID 1392666 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[C:5]1[C:10](Cl)=[CH:9][C:8]([C:12]2[C:17]([CH2:18][CH3:19])=[CH:16][CH:15]=[CH:14][C:13]=2[CH2:20][CH3:21])=[N:7][C:6]=1[CH3:22])[CH3:2].[CH3:24][S-:25].[Na+].O>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:23])[C:5]1[C:10]([S:25][CH3:24])=[CH:9][C:8]([C:12]2[C:17]([CH2:18][CH3:19])=[CH:16][CH:15]=[CH:14][C:13]=2[CH2:20][CH3:21])=[N:7][C:6]=1[CH3:22])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 4378561Sodium methanethiolateHCID 59678345Ethyl 4-chloro-6-(2,6-diethylphenyl)-2-methylnicotinate

Product 1

HCID 669940156-(2,6-Diethyl-phenyl)-2-methyl-4-methylsulfanyl-nicotinic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 4-chloro-6-(2,6-diethyl-phenyl)-2-methyl-nicotinic acid ethyl ester (200 mg, 0.60 mmol) and sodium thiomethoxide (126 mg, 1.80 mmol) in DMF (5 mL) is heated at 70° C. overnight. After cooling, water (20 mL) is added and the resulting mixture is extracted with EtOAc. The combined extracts are washed with brine, dried over sodium sulfate and concentrated. The residue is chromatographed on silica gel to give 6-(2,6-diethyl-phenyl)-2-methyl-4-methylsulfanyl-nicotinic acid ethyl ester.

Workup

  1. temperatureAfter cooling
  2. extractionthe resulting mixture is extracted with EtOAc
  3. washThe combined extracts are washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-1c4c6346f45741369d35f1c884a17b7d
Source dataset
uspto-grants-2008_03
Patent number
US07342115B2

Reaction notes

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