Hydrochloric Acid → 5-(2-Methyl-1,3-thiazol-4-yl)thiophene-2-carboxylic acid

HRID 896463Notes

Reaction equation

HRID 896463 reaction equation
[Li+].[OH-].[CH3:3][C:4]1[S:5][CH:6]=[C:7]([C:9]2[S:13][C:12]([C:14]([O:16]C)=[O:15])=[CH:11][CH:10]=2)[N:8]=1.Cl>O1CCOCC1>[CH3:3][C:4]1[S:5][CH:6]=[C:7]([C:9]2[S:13][C:12]([C:14]([OH:16])=[O:15])=[CH:11][CH:10]=2)[N:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 2819954Methyl 5-(2-methylthiazol-4-yl)thiophene-2-carboxylate

Product 1

HCID 6144675-(2-Methyl-1,3-thiazol-4-yl)thiophene-2-carboxylic acidYield 69.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Aqueous LiOH (1N, 1.5 mL) is added to a solution of methyl 5-(2-methylthiazol-4-yl)-thiophene-2-carboxylate (81 mg, 0.34 mmol) in dioxane (1 mL). The reaction is stirred at rt for 2 hr. Aqueous HCl (1N, 4 mL) is added and the resultant precipitate is collected by filtration, washed with water, and dried to give 5-(2-methylthiazol-4-yl)-thiophene-2-carboxylic acid (53 mg, 69%). 1H NMR (300 MHz, DMSO-d6) δ 8.03, 7.69, 7.59, 2.70.

Workup

  1. filtrationthe resultant precipitate is collected by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-4e0d788fc6e742d580c2f87949868d86
Source dataset
uspto-grants-2005_07
Patent number
US06919359B2

Reaction notes

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