Hydrochloric Acid → 3-Ethylisothiazole-4-carboxylic acid

HRID 869461Notes

Reaction equation

HRID 869461 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.[CH2:13]1COCC1.CO.O>>[CH2:1]([C:2]1[C:6]([C:7]([OH:9])=[O:8])=[CH:5][S:4][N:3]=1)[CH3:13]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21892291Methanol tetrahydrofuran waterHCID 289502153-Methylisothiazole-4-carboxylate

Product 1

HCID 836821333-Ethylisothiazole-4-carboxylic acid

Conditions

Temperature
40 °C

Procedure

To a solution of 3-methylisothiazole-4-carboxylate (G-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 ethylisothiazole-4-carboxylic acid (G-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-adcbc5911ddf4ea7a0d607dc13177ec8
Source dataset
uspto-grants-2015_03
Patent number
US08969363B2

Reaction notes

Loading…