Sodium hydride → Ethyl 2-methyl-4-sulfanyl-1,3-thiazole-5-carboxylate

HRID 925276Notes

Reaction equation

HRID 925276 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([CH3:11])=[N:8][C:7]=1[S:12]C(=O)N(C)C)=[O:5])[CH3:2].[H-].[Na+]>CO>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([CH3:11])=[N:8][C:7]=1[SH:12])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 150771294-[(Dimethyl-carbamoyl)sulfanyl]-2-methyl-thiazole-5-carboxylic acid ethyl ester

Product 1

HCID 15077130Ethyl 2-methyl-4-sulfanyl-1,3-thiazole-5-carboxylateYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 4-[(dimethyl-carbamoyl)sulfanyl]-2-methyl-thiazole-5-carboxylic acid ethyl ester (0.84 g, 3.06 mmol) in MeOH (30 ml) is added sodium hydride (60% oil dispersion) (0.4 g, 10.1 mmol). The mixture is refluxed for 1 h under an atmosphere of nitrogen and concentrated. The residue is treated with 1M hydrochloric acid and extracted with EtOAc (3×30 ml). The combined organic layers are washed with brine (30 ml), dried over sodium sulfate and concentrated to give 4-mercapto-2-methyl-thiazole-5-carboxylic acid ethyl ester (0.58 g, 2.83 mmol, 94%), which is used in the next step without further purification.

Workup

  1. temperatureThe mixture is refluxed for 1 h under an atmosphere of nitrogen
  2. concentrationconcentrated
  3. additionThe residue is treated with 1M hydrochloric acid
  4. extractionextracted with EtOAc (3×30 ml)
  5. washThe combined organic layers are washed with brine (30 ml)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d051d4dc5c5540bfb2e952566b76ff12
Source dataset
uspto-grants-2016_03
Patent number
US09284286B2

Reaction notes

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