Sodium Hydroxide → 5-Phenylsulfanyl-[1,3,4]thiadiazole-2-carboxylic acid

HRID 2298367Notes

Reaction equation

HRID 2298367 reaction equation
C([O:3][C:4]([C:6]1[S:7][C:8]([S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:9][N:10]=1)=[O:5])C.[OH-].[Na+]>CCO>[C:12]1([S:11][C:8]2[S:7][C:6]([C:4]([OH:5])=[O:3])=[N:10][N:9]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 699746815-Phenylsulfanyl-[1,3,4]thiadiazole-2-carboxylic acid ethyl ester

Product 1

HCID 181809825-Phenylsulfanyl-[1,3,4]thiadiazole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The 5-phenylsulfanyl-[1,3,4]thiadiazole-2-carboxylic acid ethyl ester from Step 64a (1.0 g, 3.76 mmol, 1 eq) is dissolved in EtOH (40 mL), and cooled in an ice bath. To this, 2N NaOH (1.88 mL 3.76 mmol, 1 eq) is added drop wise. The sodium salt of the acid precipitates out of solution. The reaction mixture is concentrated in vacuo to give a white crystalline product. The reaction mixture is carried through to the next step in its crude form to make the acid chloride. MS (ESI) for C9H6N2S2O2 m/z 237.0 (M−M)−.

Workup

  1. temperaturecooled in an ice bath
  2. customThe sodium salt of the acid precipitates out of solution
  3. concentrationThe reaction mixture is concentrated in vacuo
  4. customto give a white crystalline product

Sources & evidence

ORD record
ord-90c320f724c24fe5b82415c5126d7588
Source dataset
uspto-grants-2002_12
Patent number
US06492385B2

Reaction notes

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