Water → Methyl 4-(2-aminothiazol-4-yl)benzoate

HRID 1061000Notes

Reaction equation

HRID 1061000 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1)=O.[NH2:15][C:16]([NH2:18])=[S:17].C(=O)([O-])[O-].[Na+].[Na+].O>C(O)(C)C>[NH2:18][C:16]1[S:17][CH:2]=[C:3]([C:5]2[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=2)[N:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2723790ThioureaHCID 13612771Methyl 4-(2-bromoacetyl)benzoate

Product 1

HCID 2060012Methyl 4-(2-aminothiazol-4-yl)benzoate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

At room temperature, methyl 4-bromoacetylbenzoate (1.00 g) and thiourea (296 mg) were dissolved in isopropanol (100 ml), followed by heating under reflux for 15 minutes. Under stirring at the same temperature, anhydrous sodium carbonate (206 mg) was added to the reaction mixture. The resulting mixture was heated under reflux for 20 minutes. After completion of the reaction, water (50 ml) was added under ice cooling and the solid so precipitated was collected by filtration. The solid was dissolved in water and dichloromethane. The organic layer so separated was dried over anhydrous sodium sulfate. The solvent was then distilled off. The pale yellow solid so precipitated was washed with ether, whereby the title compound (634 mg, 70%) was obtained.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 15 minutes
  3. additionwas added to the reaction mixture
  4. temperatureThe resulting mixture was heated
  5. temperatureunder reflux for 20 minutes
  6. additionwas added under ice cooling
  7. customthe solid so precipitated
  8. filtrationwas collected by filtration
  9. dissolutionThe solid was dissolved in water
  10. customThe organic layer so separated
  11. dry with materialwas dried over anhydrous sodium sulfate
  12. distillationThe solvent was then distilled off
  13. customThe pale yellow solid so precipitated
  14. washwas washed with ether, whereby the title compound (634 mg, 70%)
  15. customwas obtained

Sources & evidence

ORD record
ord-8244e37be0a24c04aec173e8cbf8511c
Source dataset
uspto-grants-2003_02
Patent number
US06525042B1

Reaction notes

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