Methanol → 4-(2-Amino-1,3-thiazol-4-yl)benzoic acid

HRID 1061001Notes

Reaction equation

HRID 1061001 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:16]=[CH:15][C:10]([C:11]([O:13]C)=[O:12])=[CH:9][CH:8]=2)[N:6]=1.O1CCCC1.CO.[OH-].[Na+]>CN(C)C=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]([C:11]([OH:13])=[O:12])=[CH:15][CH:16]=2)[N:6]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 2060012Methyl 4-(2-aminothiazol-4-yl)benzoate

Product 1

HCID 6131794-(2-Amino-1,3-thiazol-4-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

At room temperature, methyl 4-(2-aminothiazol-4-yl)benzoate (300 mg) was suspended in a mixed solvent of tetrahydrofuran (5 ml) and methanol (5 ml), followed by the addition of a 1N aqueous sodium hydroxide solution (10 ml). The resulting mixture was stirred for one hour. To the reaction mixture, N,N-dimethylformamide (5 ml) was added, followed by heating under reflux for 6 hours. After completion of the reaction, the solvent was distilled off. To the residue, water and 1N hydrochloric acid were added successively and the pale yellow solid so precipitated was collected by filtration, whereby the title compound (229 mg, 69%) was obtained as a pale yellow solid.

Workup

  1. customAt room temperature
  2. temperatureby heating
  3. temperatureunder reflux for 6 hours
  4. customAfter completion of the reaction
  5. distillationthe solvent was distilled off
  6. additionTo the residue, water and 1N hydrochloric acid were added successively
  7. customthe pale yellow solid so precipitated
  8. filtrationwas collected by filtration, whereby the title compound (229 mg, 69%)
  9. customwas obtained as a pale yellow solid

Sources & evidence

ORD record
ord-8feb5b1b1c0546ad9e1018ccc7bad5ae
Source dataset
uspto-grants-2003_02
Patent number
US06525042B1

Reaction notes

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