Water → N-[5-Phenyl-4-(3-pyridyl)-1,3-thiazol-2-yl]acetamide

HRID 1167655Notes

Reaction equation

HRID 1167655 reaction equation
[C:1]1([C:7]2[S:11][C:10]([NH2:12])=[N:9][C:8]=2[C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:19](Cl)(=[O:21])[CH3:20].O>CN(C)C(=O)C>[C:1]1([C:7]2[S:11][C:10]([NH:12][C:19](=[O:21])[CH3:20])=[N:9][C:8]=2[C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6367Acetyl chlorideHCID 9794996[5-Phenyl-4-(3-pyridyl)-1,3-thiazol-2-yl]amine

Product 1

HCID 22993726N-[5-Phenyl-4-(3-pyridyl)-1,3-thiazol-2-yl]acetamideYield 59%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of [5-phenyl-4-(3-pyridyl)-1,3-thiazol-2-yl]amine (1.10 g, 4.34 mmol) in N,N-dimethylacetamide (20 mL) was added acetyl chloride (680 mg, 8.68 mmol) and stirred at 80° C. for 3 h. Water was added to the reaction mixture and extracted with ethyl acetate twice. The combined organic phases were washed with water, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was recrystallized from chloroform-ethyl ether to give the title compound (750 mg, yield 59%).

Workup

  1. extractionextracted with ethyl acetate twice
  2. washThe combined organic phases were washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from chloroform-ethyl ether

Sources & evidence

ORD record
ord-834c340d43ad4baeb20aab275f52b97d
Source dataset
uspto-grants-2003_09
Patent number
US06620825B1

Reaction notes

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