Hydrochloric Acid → 4-Methyl-1,2,3-thiadiazole-5-carboxylic acid

HRID 649864

Reaction equation

HRID 649864 reaction equation
C[O:2][C:3]([C:5]1[S:9][N:8]=[N:7][C:6]=1[CH3:10])=[O:4].[OH-].[Na+].Cl>CO>[CH3:10][C:6]1[N:7]=[N:8][S:9][C:5]=1[C:3]([OH:4])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 7576666Methyl 4-methyl-1,2,3-thiadiazole-5-carboxylate

Product 1

HCID 13819924-Methyl-1,2,3-thiadiazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Methyl-[1,2,3]thiadiazole-5-carboxylic acid methyl ester (1.7 g) is dissolved in methanol (15 mL) and treated with 1N sodium hydroxide (16 mL). After stirring at room temperature for 1 hour, the reaction is treated with concentrated hydrochloric acid (1.5 mL) and concentrated under reduced pressure. The resulting turbid aqueous layer is extracted twice with diethyl ether and the pooled organic layers are dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the desired compound as a white powder.

Workup

  1. concentrationconcentrated under reduced pressure
  2. extractionThe resulting turbid aqueous layer is extracted twice with diethyl ether
  3. dry with materialthe pooled organic layers are dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3a3e4431c7854b1cb2bf23ba0601180c
Source dataset
uspto-grants-2001_08
Patent number
US06271236B1

Linked notes

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