Sodium Hydroxide → HCID 59278483, compound

HRID 559672Notes

Reaction equation

HRID 559672 reaction equation
C([O:3][C:4]([C:6]1[O:10][C:9]([S:11][CH2:12]C)=[N:8][CH:7]=1)=[O:5])C.[OH-].[Na+]>C(O)C.O>[CH3:12][S:11][C:9]1[O:10][C:6]([C:4]([OH:5])=[O:3])=[CH:7][N:8]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66727531HCID 66727531, compound

Product 1

HCID 59278483HCID 59278483, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-ethylsulfanyl-oxazole-5-carboxylic acid ethyl ester (4.6 g, 24.57 mmol) in ethanol (100 mL) was added a 2 N solution of sodium hydroxide (37 mL, 74 mmol) in water. The mixture was heated at 80° C. for 4 hours and then concentrated in vacuo to remove the ethanol. The remaining aqueous solution was then acidified with 1 N HCl and extracted with ethyl acetate (4×30 mL). The combined organic layers were washed with brine (2×100 mL), dried over sodium sulfate and concentrated to afford 2-methylsulfanyl-oxazole-5-carboxylic acid.

Workup

  1. concentrationconcentrated in vacuo
  2. customto remove the ethanol
  3. extractionextracted with ethyl acetate (4×30 mL)
  4. washThe combined organic layers were washed with brine (2×100 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-675021e5951549c39ed76eabee39b8cd
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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