4-Nitrophenol → HCID 69205616, compound

HRID 30654Notes

Reaction equation

HRID 30654 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.Cl[CH2:13][C:14]1[N:15]=[CH:16][S:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:13][C:14]2[N:15]=[CH:16][S:17][CH:18]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 9804-NitrophenolHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 27632894-(Chloromethyl)-1,3-thiazole hydrochloride

Product 1

HCID 69205616HCID 69205616, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-nitrophenol (3.92 g), 4-chloromethyl-1,3-thiazole hydrochloride (4.0 g), potassium carbonate (8.13 g) and N,N-dimethylformamide (100 mL) was stirred at room temperature for 40 hrs. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate-tetrahydrofuran. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give 4-[(4-nitrophenoxy)methyl]-1,3-thiazole as colorless crystals (3.38 g, yield 61%). Recrystallization thereof from ethyl acetate-hexane gave colorless prism crystals. melting point: 175-176° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate-tetrahydrofuran
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-957c5dd231234aeaac29b49f92f5704d
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

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