Dimethylformamide → HCID 89486244, compound

HRID 2401694Notes

Reaction equation

HRID 2401694 reaction equation
F[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[O:9][C:10]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:11]=2[CH:12]=1.[Na].[CH2:22]([SH:24])[CH3:23].CN(C=O)C>O>[CH2:22]([S:24][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[O:9][C:10]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:11]=2[CH:12]=1)[CH3:23]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 45051917Sodium ethanethiolHCID 86680834HCID 86680834, compound

Product 1

HCID 89486244HCID 89486244, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.25 g of 3-fluoro-4-[5-(trifluoromethyl)benzofuran-2-yl]pyridine, 0.11 g of ethyl mercaptan sodium salt and 3.5 ml of DMF was stirred under ice-cooling for 2 hours. Water was added to the reaction mixture, and the mixture was extracted twice with ethyl acetate. The organic layers were combined and washed with water and saturated brine and dried over magnesium sulfate, then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.26 g of 3-ethylthio-4-[5-(trifluoromethyl)benzofuran-2-yl]pyridine (hereinafter, referred to as “Present Active Compound 12”).

Workup

  1. temperaturecooling for 2 hours
  2. extractionthe mixture was extracted twice with ethyl acetate
  3. washwashed with water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4bb3e0a748344965b3c56cba734de511
Source dataset
uspto-grants-2014_08
Patent number
US08796306B2

Reaction notes

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