Sodium Hydroxide → 4-Ethoxycarbonyl-2-methylthiothiazole-5-carboxylic acid

HRID 5329

Reaction equation

HRID 5329 reaction equation
[OH-].[Na+].[CH3:3][S:4][C:5]1[S:6][C:7]([C:15]([O:17]CC)=[O:16])=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:9]=1>O.C(O)C.O>[CH2:13]([O:12][C:10]([C:8]1[N:9]=[C:5]([S:4][CH3:3])[S:6][C:7]=1[C:15]([OH:17])=[O:16])=[O:11])[CH3:14]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 15009537Diethyl 2-methylthiothiazole-4,5-dicarboxylate

Product 1

HCID 150095384-Ethoxycarbonyl-2-methylthiothiazole-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 19096565Water ethanolSolvent

Procedure

At room temperature, a solution of 1.10 g (27.5 mmol) of sodium hydroxide in 10 ml of water was added over a period of one hour to a solution of 7.00 g (25 mmol) of diethyl 2-methylthiothiazole-4,5-dicarboxylate in 100 ml of ethanol/water (2:1). The mixture was stirred for one hour, the solvent mixture was then removed under reduced pressure, the residue was taken up in 100 ml of water, the solution was extracted once with 50 ml of diethyl ether, and the aqueous phase was acidified with concentrated hydrochloric acid. The precipitated product was filtered off and dried.

Workup

  1. customthe solvent mixture was then removed under reduced pressure
  2. extractionthe solution was extracted once with 50 ml of diethyl ether
  3. filtrationThe precipitated product was filtered off
  4. customdried

Sources & evidence

ORD record
ord-cac5b60f283041dda7c7abbd2044a9b6
Source dataset
uspto-grants-1993_09
Patent number
US05244867

Linked notes

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