Sodium Hydroxide → 4-Mercapto-thiazole-5-carboxylic acid methyl ester

HRID 925270Notes

Reaction equation

HRID 925270 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]([C:7]1[S:11][CH:10]=[N:9][C:8]=1[S:12]CCC(OC)=O)=[O:6]>CO>[CH3:3][O:4][C:5]([C:7]1[S:11][CH:10]=[N:9][C:8]=1[SH:12])=[O:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 867201684-(2-Methoxycarbonyl-ethylsulfanyl)-thiazole-5-carboxylic acid methyl ester

Product 1

HCID 867201674-Mercapto-thiazole-5-carboxylic acid methyl esterYield 64.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

Sodium hydroxide (0.29 g, 7.27 mmol) is added to a solution of 4-(2-methoxycarbonyl-ethylsulfanyl)-thiazole-5-carboxylic acid methyl ester (2.0 g, 7.27 mmol) in MeOH (30 ml). The mixture is refluxed at 70-80° C. for 1 h and then concentrated in vacuo. The residue is dissolved in EtOAc/water (1:1) (80 ml) and the pH is adjusted to 2 with 2M hydrochloric acid. The organic layer is dried over sodium sulfate and concentrated yielding 4-mercapto-thiazole-5-carboxylic acid methyl ester (0.82 g, 4.67 mmol, 46%).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue is dissolved in EtOAc/water (1:1) (80 ml)
  3. dry with materialThe organic layer is dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b642bab2698640be942e421b330687bb
Source dataset
uspto-grants-2016_03
Patent number
US09284286B2

Reaction notes

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