4-Nitrophenol → 2-Ethyl-4-[(4-nitrophenoxy)methyl]-1,3-thiazole

HRID 30655Notes

Reaction equation

HRID 30655 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl[CH2:12][C:13]1[N:14]=[C:15]([CH2:18][CH3:19])[S:16][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH2:18]([C:15]1[S:16][CH:17]=[C:13]([CH2:12][O:10][C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[N:14]=1)[CH3:19]

Participants

6

Reactant 4

HCID 9804-NitrophenolHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 162279604-(Chloromethyl)-2-ethyl-1,3-thiazole

Product 1

HCID 458676682-Ethyl-4-[(4-nitrophenoxy)methyl]-1,3-thiazoleYield 35%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-nitrophenol (5.48 g), 4-chloromethyl-2-ethyl-1,3-thiazole (7.40 g), potassium carbonate (5.45 g) and N,N-dimethylformamide (50 mL) was stirred at room temperature for 15 hrs. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with 1N aqueous sodium hydroxide solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give 2-ethyl-4-[(4-nitrophenoxy)methyl]-1,3-thiazole as colorless crystals (3.60 g, yield 35%) from a fraction eluted with hexane-ethyl acetate (4:1, v/v). Recrystallization thereof from ethyl acetate-hexane gave colorless prism crystals. melting point: 79-80° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed successively with 1N aqueous sodium hydroxide solution and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b0a9153c69754dd59eb5f2e0f8414f3f
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

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