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

HRID 990861Notes

Reaction equation

HRID 990861 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-0f12a2b289194216a214376bab8bee67
Source dataset
uspto-grants-2002_10
Patent number
US06462055B2

Reaction notes

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