Hydrochloric Acid → 3-Methyl-1,2-thiazole-4-carboxylic acid

HRID 1773480Notes

Reaction equation

HRID 1773480 reaction equation
[CH3:1][C:2]1[C:6]([C:7]([O-:9])=[O:8])=[CH:5][S:4][N:3]=1.[OH-].[Na+].Cl>C1COCC1.CO.O>[CH3:1][C:2]1[C:6]([C:7]([OH:9])=[O:8])=[CH:5][S:4][N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 289502153-Methylisothiazole-4-carboxylate

Product 1

HCID 5886923-Methyl-1,2-thiazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 3-methylisothiazole-4-carboxylate (C-3) (4.73 g, 30.1 mmol) in THF-MeOH—H2O (2:1:1, 50 mL), NaOH (3.61 g, 90.3 mmol) is added and the resulting mixture is stirred at 40° C. for 16 h. The mixture is allowed to cool to RT and then acidified with concentrated HCl to adjust the pH to 2-3. The precipitate is collected by filtration, rinsed with water and dried in vacuo to afford the product, 3-methylisothiazole-4-carboxylic acid (C-4).

Workup

  1. temperatureto cool to RT
  2. filtrationThe precipitate is collected by filtration
  3. washrinsed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-85414263cc8a452096b59a5eb3d996d2
Source dataset
uspto-grants-2016_02
Patent number
US09255108B2

Reaction notes

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