Sodium Bicarbonate → 2-(2-Aminothiazol-4-yl)-4-chlorophenol

HRID 644461Notes

Reaction equation

HRID 644461 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[OH:12])=O.[NH2:13][C:14]([NH2:16])=[S:15].C(=O)([O-])O.[Na+]>C(O)C>[NH2:16][C:14]1[S:15][CH:2]=[C:3]([C:5]2[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=2[OH:12])[N:13]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2723790ThioureaHCID 27568852-Bromo-5'-chloro-2'-hydroxyacetophenone

Product 1

HCID 47154202-(2-Aminothiazol-4-yl)-4-chlorophenolYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-1-(5-chloro-2-hydroxyphenyl)ethanone (156.9 mg, 0.63 mmol), thiourea (47.9 mg, 0.63 mmol) and ethanol (3 mL) was refluxed for 2 hours. After the reaction mixture was cooled to room temperature, it was poured into saturated sodium hydrogen carbonate solution and extracted with ethyl acetate. After the ethyl acetate layer was washed with brine and dried over anhydrous sodium sulfate, the residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=2:1) to give the title compound (98.6 mg, 64.5%) as a light yellowish white powder.

Workup

  1. temperaturewas refluxed for 2 hours
  2. extractionextracted with ethyl acetate
  3. washAfter the ethyl acetate layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe residue obtained by evaporation of the solvent under reduced pressure
  6. customwas purified by column chromatography on silica gel (n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-7d7ace59f7ba422c8b430a046831d9f9
Source dataset
uspto-grants-2010_04
Patent number
US07700655B2

Reaction notes

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