Sodium Hydroxide → 2-(2-Methylimidazo[2,1-b][1,3,4]thiadiazol-6-yl)acetic acid

HRID 1913420Notes

Reaction equation

HRID 1913420 reaction equation
C([O:3][C:4](=[O:15])[CH2:5][C:6]1[N:7]=[C:8]2[N:12]([CH:13]=1)[N:11]=[C:10]([CH3:14])[S:9]2)C.[OH-].[Na+]>CCO>[CH3:14][C:10]1[S:9][C:8]2=[N:7][C:6]([CH2:5][C:4]([OH:15])=[O:3])=[CH:13][N:12]2[N:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13426063Ethyl 2-(2-methylimidazo[2,1-b][1,3,4]thiadiazol-6-yl)acetate

Product 1

HCID 134260662-(2-Methylimidazo[2,1-b][1,3,4]thiadiazol-6-yl)acetic acidYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To (2-methyl-imidazo[2,1-b][1,3,4]thiadiazol-6-yl)acetic acid ethyl ester (4.0 g, 17.76 mmol) in 30 mL EtOH was added aqueous NaOH (1M, 19.5 mL) and the mixture was stirred at room temperature for 1 hour or until LC-MS showed complete consumption of starting material. To the mixture was added Amberlyst 15 (wet) ion-exchange resin (Aldrich) until the pH reached 5. The resin was removed by filtration and the filtrate was concentrated to obtain 1.7 g (50%) of the title compound (SM-1ae). Further purification was performed by trituration with water and ethyl ester to obtain a white solid. MS (ES+) 198.1 (M+H)+ 1H NMR (DMSO-d6) δ 2.66 (s, 3H), 3.53 (s, 2H), 7.86 (s, 1H), 12.31 (br s, 1H).

Workup

  1. customconsumption of starting material
  2. additionTo the mixture was added Amberlyst 15 (wet) ion-exchange resin (Aldrich) until the pH
  3. customThe resin was removed by filtration
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-99c98a44721740d0bca4526cb1eb9761
Source dataset
uspto-grants-2013_12
Patent number
US08609680B2

Reaction notes

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