2-Bromo-3-hydroxyacrylaldehyde → 2-(Pyridin-2-ylamino)thiazole-5-carbaldehyde

HRID 6862

Reaction equation

HRID 6862 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]([NH2:10])=[S:9].Br[C:12](=[CH:15]O)[CH:13]=[O:14].C([O-])(=O)C.[Na+]>CC(C)=O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[S:9][C:12]([CH:13]=[O:14])=[CH:15][N:10]=1

Participants

5

Reactant 3

HCID 1705652-Bromo-3-hydroxyacrylaldehydeHCID 517045Sodium AcetateHCID 14904911-(2-Pyridyl)-2-thiourea

Product 1

HCID 220190582-(Pyridin-2-ylamino)thiazole-5-carbaldehydeYield 52%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
75 °C

Procedure

To a solution of 1-(2-pyridyl)-2-thiourea (765 mg, 5.0 mmol) in acetone (14 mL) was added slowly 2-bromo-3-hydroxypropenal (755 mg, 5.0 mmol, for preparation see J. Org. Chem. 28, 3243, 1963) in acetone (14 mL) over a period of 5 min. After stirring for 1.5 h, a precipitate formed. The solids were separated, washed with acetone (10 mL) and then taken into mixed solvent (ethanol/water=1/1, 9 mL). To this suspension was added sodium acetate (1.23 g, 15.0 mmol) and the resulting mixture was heated at 75° C. for 1 h. After cooling to RT, the mixture was filtered and the solids were washed with water (10 mL), and dried in vacuo to provide compound A, 2-(pyridin-2-ylamino)-thiazole-5-carbaldehyde (533 mg, 52%) as a solid. LC/MS; (M+H)+=206

Workup

  1. customa precipitate formed
  2. customThe solids were separated
  3. washwashed with acetone (10 mL)
  4. additioninto mixed solvent (ethanol/water=1/1, 9 mL)
  5. temperatureAfter cooling to RT
  6. filtrationthe mixture was filtered
  7. washthe solids were washed with water (10 mL)
  8. customdried in vacuo

Sources & evidence

ORD record
ord-c0f346fd6672465c92d63410e95e866a
Source dataset
uspto-grants-2006_08
Patent number
US07084160B2

Linked notes

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