Sodium Hydroxide → 2-Methoxy-1,3-thiazole-5-carboxylic acid

HRID 1480388Notes

Reaction equation

HRID 1480388 reaction equation
Cl[C:2]1[S:3][C:4]([C:7]([O:9]C(C)(C)C)=[O:8])=[CH:5][N:6]=1.[CH3:14][O-:15].[Na+].[OH-].[Na+]>CC#N.CO>[CH3:14][O:15][C:2]1[S:3][C:4]([C:7]([OH:9])=[O:8])=[CH:5][N:6]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 10942334Sodium MethoxideHCID 24229786tert-Butyl 2-chloro-1,3-thiazole-5-carboxylate

Product 1

HCID 164948972-Methoxy-1,3-thiazole-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of tert-butyl 2-chlorothiazole-5-carboxylate (100 mg, 0.455 mmol) in MeCN (880 μl) and MeOH (880 ul) was added 5.4M NaOMe in MeOH (337 μl, 1.821 mmol) followed by 2M NaOH (881 μl, 1.762 mmol). The reaction mixture was heated to 80° C. overnight and, after cooling to RT, the mixture was evaporated under reduced pressure. The residue was acidified with a minimal volume of 6M aqueous hydrochloric acid. The resulting precipitate was filtered, washed with water and dried in a high vacuum oven overnight to afford the title compound;

Workup

  1. temperatureafter cooling to RT
  2. customthe mixture was evaporated under reduced pressure
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water
  5. customdried in a high vacuum oven overnight

Sources & evidence

ORD record
ord-d54a00cbb60c4c57bb0975f2edfc08d4
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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