Hydrochloric Acid → Pyridin-3-yl-4-trifluoromethyl-thiazole-5-carboxylic acid

HRID 2199195Notes

Reaction equation

HRID 2199195 reaction equation
C([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[N:8][C:7]=1[C:17]([F:20])([F:19])[F:18])=[O:5])C.[OH-].[Na+].Cl.O>CO>[N:13]1[CH:14]=[CH:15][CH:16]=[C:11]([C:9]2[S:10][C:6]([C:4]([OH:5])=[O:3])=[C:7]([C:17]([F:19])([F:20])[F:18])[N:8]=2)[CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 595808352-Pyridin-3-yl-4-trifluoromethyl-thiazole-5-carboxylic acid ethyl ester

Product 1

HCID 59580876Pyridin-3-yl-4-trifluoromethyl-thiazole-5-carboxylic acidYield 58.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-pyridin-3-yl-4-trifluoromethyl-thiazole-5-carboxylic acid ethyl ester (13.9 g, 46 mmol, ca. 85% pure) in methanol (150 mL) was added an aqueous solution of sodium hydroxide (total volume 75 mL, 140 mmol), and the mixture was stirred for 40 min. Upon addition of 2 N HCl (70 mL, ca pH=3) to the reaction mixture, a precipitate was formed. Water (300 mL) was then added and the heterogeneous mixture was filtered under reduced pressure. The precipitate was rinsed further with water and dried in vacuo to give the desired product as an off-white solid (7.37 g, 58%): mp 209° C.; 1H NMR (300 MHz, DMSO-d6) δ 9.21 (d, J=2.5 Hz, 1H), 8.77 (dd, J=4.9, 1.7 Hz, 1H), 8.41 (dt, J=8.0, 1.7 Hz, 1H), 7.60 (dd, J=8.0, 4.9 Hz, 1H), 3.4 (br s, 1H); ESIMS m/z 276.2 (M+1).

Workup

  1. customa precipitate was formed
  2. filtrationthe heterogeneous mixture was filtered under reduced pressure
  3. washThe precipitate was rinsed further with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-9048bdc5190042569dc867d8dd0c1716
Source dataset
uspto-grants-2016_06
Patent number
US09357780B2

Reaction notes

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