Hydrochloric Acid → 2-(2,6-Difluorophenyl)-1,3-thiazole-4-carboxylic acid

HRID 705222Notes

Reaction equation

HRID 705222 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[S:10][CH:11]=[C:12]([C:14]([O:16]CC)=[O:15])[N:13]=1.[Li+].[OH-].Cl>C1COCC1.CO>[F:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[C:9]1[S:10][CH:11]=[C:12]([C:14]([OH:16])=[O:15])[N:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59455697Ethyl 2-(2,6-difluorophenyl)thiazole-4-carboxylate

Product 1

HCID 242784542-(2,6-Difluorophenyl)-1,3-thiazole-4-carboxylic acidYield 88%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(2,6-difluorophenyl)thiazole-4-carboxylate (1.0 eq.) in 2:1 THF/MeOH (0.17 M) was added 1.0 M LiOH (2.0 eq.). After standing for 16 hours, 1.0 M HCl (2.0 eq.) was added and the THF/MeOH was removed in vacuo. The resulting solid was filtered, rinsed with H2O and dried, yielding 2-(2,6-difluorophenyl)thiazole-4-carboxylic acid (88%) as a crusty solid. LCMS (m/z): 251.1 (MH+); LC Rt=2.68 min.

Workup

  1. customthe THF/MeOH was removed in vacuo
  2. filtrationThe resulting solid was filtered
  3. washrinsed with H2O
  4. customdried

Sources & evidence

ORD record
ord-9a957cbf40d74df38a7965aeef82f16d
Source dataset
uspto-grants-2015_11
Patent number
US09173883B2

Reaction notes

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