Dimethylformamide → 2-[3-(Methylthio)pyridin-4-yl]-5-(trifluoromethyl)benzothiazole

HRID 402332Notes

Reaction equation

HRID 402332 reaction equation
F[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:11]=2[N:12]=1.[Na].[CH3:22][SH:23].CN(C=O)C>O>[CH3:22][S:23][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:11]=2[N:12]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 45051789Methylmercaptan sodiumHCID 671137612-(3-Fluoropyridin-4-yl)-5-(trifluoromethyl)benzothiazole

Product 1

HCID 671139332-[3-(Methylthio)pyridin-4-yl]-5-(trifluoromethyl)benzothiazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.30 g of 2-(3-fluoropyridin-4-yl)-5-(trifluoromethyl)benzothiazole, 0.14 g of methylmercaptan sodium salt and 3 ml of DMF was stirred at room temperature for 20 minutes. To the reaction mixture was added water, and the resultant mixture was extracted with ethyl acetate three times. The combined organic layers were washed with water and saturated saline, dried over magnesium sulfate, then, concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, to obtain 2-[3-(methylthio)pyridin-4-yl]-5-(trifluoromethyl)benzothiazole (hereinafter, referred to as the present compound 5).

Workup

  1. extractionthe resultant mixture was extracted with ethyl acetate three times
  2. washThe combined organic layers were washed with water and saturated saline
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f51d624970024d0eb930e131fc92d8bc
Source dataset
uspto-grants-2014_06
Patent number
US08742112B2

Reaction notes

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