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

HRID 352729
Notes
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Reaction equation

HRID 352729 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6228Dimethylformamide
Solvent

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-62ce097c977e4e46aed2f9398ef2e822
Source dataset
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06747023B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes