Dimethyl Sulfoxide → 2-(3-Fluoropyridin-4-yl)-5-(trifluoromethyl)benzothiazole

HRID 402330

Reaction equation

HRID 402330 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[SH:13].[F:14][C:15]1[CH:22]=[N:21][CH:20]=[CH:19][C:16]=1[CH:17]=O.C(N(C(C)C)C(C)C)C.CS(C)=O>O>[F:14][C:15]1[CH:22]=[N:21][CH:20]=[CH:19][C:16]=1[C:17]1[S:13][C:4]2[CH:5]=[CH:6][C:7]([C:9]([F:10])([F:11])[F:12])=[CH:8][C:3]=2[N:2]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 27346782-Amino-4-(trifluoromethyl)benzenethiol hydrochlorideHCID 27630033-Fluoroisonicotinaldehyde

Product 1

HCID 671137612-(3-Fluoropyridin-4-yl)-5-(trifluoromethyl)benzothiazoleYield 60.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 2.3 g of 2-amino-4-(trifluoromethyl)-benzenethiol hydrochloride, 1.25 g of 3-fluoroisonicotinaldehyde, 1.29 g of N-ethyldiisopropylamine and 10 ml of DMSO was stirred for 5 hours at 170° C. The reaction mixture was cooled down to room temperature. To the reaction mixture was added water, and the resultant mixture was extracted with ethyl acetate twice. 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 1.79 g of 2-(3-fluoropyridin-4-yl)-5-(trifluoromethyl)benzothiazole (hereinafter, referred to as the present compound 1).

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. extractionthe resultant mixture was extracted with ethyl acetate twice
  3. washThe combined organic layers were washed with water and saturated saline
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-81783412adec46318b8f5c9a7909478f
Source dataset
uspto-grants-2014_06
Patent number
US08742112B2

Linked notes

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