Ethyl Acetate → 4-(3-Nitrophenyl)-2-(pyridin-3-yl)thiazole

HRID 2086769Notes

Reaction equation

HRID 2086769 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=1)=O.[C:14]([C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)(=[S:16])[NH2:15].C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>C(O)C>[N+:11]([C:7]1[CH:6]=[C:5]([C:3]2[N:15]=[C:14]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[S:16][CH:2]=2)[CH:10]=[CH:9][CH:8]=1)([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 752132-Bromo-1-(3-nitrophenyl)ethan-1-oneHCID 516892Sodium BicarbonateHCID 737155Thionicotinamide

Product 1

HCID 7384914-(3-Nitrophenyl)-2-(pyridin-3-yl)thiazoleYield 68.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-3′-nitroacetophenone (3.66 g) and 3-thiocarbamoylpyridine (2.07 g) in ethanol (40 ml) was refluxed for 1 hour. The reaction mixture was poured into a mixture of ethyl acetate and an aqueous sodium bicarbonate solution. The organic phase was washed with brine, dried over magnesium sulfate and concentrated. The resultant solid was collected and washed with isopropyl ether to give 4-(3-nitrophenyl)-2-(pyridin-3-yl)thiazole (2.91 g).

Workup

  1. temperaturewas refluxed for 1 hour
  2. washThe organic phase was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe resultant solid was collected
  6. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-3d90954391324cac836ec50f07c70c0b
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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