Hydrochloric Acid → 5-(3-Methoxypropyl)-2-phenylthiazole-4-carboxylic acid

HRID 1799110Notes

Reaction equation

HRID 1799110 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][C:7]=1[C:17]([O:19]CC)=[O:18].[Li+].[OH-].Cl>C1COCC1.CO.O.[Cl-].[Na+].O>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][C:7]=1[C:17]([OH:19])=[O:18]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67425119Ethyl 5-(3-methoxypropyl)-2-phenylthiazole-4-carboxylate

Product 1

HCID 585519025-(3-Methoxypropyl)-2-phenylthiazole-4-carboxylic acidYield 99.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Ethyl 5-(3-methoxypropyl)-2-phenylthiazole-4-carboxylate (26.3 g, 76.1 mmol) was dissolved in THF/MeOH (1:1, 300 mL) and a solution of LiOH (3.6 g, 152 mmol) in H2O (75 mL) was added. The reaction was stirred for ˜5 h and the pH adjusted to ˜3 by the addition of 3N HCl. The mixture was poured into brine and extracted with EtOAc. The combined organics were washed with brine, dried (MgSO4) and concentrated to give 5-(3-methoxypropyl)-2-phenylthiazole-4-carboxylic acid (21 g, 99% yield) as a tan solid.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organics were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0ef7fdcf757c43ac828dc22457ef8df8
Source dataset
uspto-grants-2013_01
Patent number
US08343997B2

Reaction notes

Loading…