2-Nitrophenol → 4-[(2-Nitrophenoxy)methyl]-2-phenylthiazole

HRID 1761673Notes

Reaction equation

HRID 1761673 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-:3])=[O:2].Cl.Cl[CH2:13][C:14]1[N:15]=[C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[S:17][CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O.[I-].[K+]>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH2:13][C:14]1[N:15]=[C:16]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[S:17][CH:18]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 69472-NitrophenolHCID 10796Cesium carbonateHCID 162436754-(Chloromethyl)-2-phenyl-1,3-thiazole hydrochloride

Product 1

HCID 47946204-[(2-Nitrophenoxy)methyl]-2-phenylthiazoleYield 67%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 180AcetoneSolvent

Procedure

To a solution of 10.7 g (0.08 mol) of 2-nitrophenol in 500 ml of acetone are added 19.0 g (0.08 mol) of 4-chloromethyl-2-phenylthiazole hydrochloride, 26.3 g (0.08 mol) of cesium carbonate, and 0.5 g of potassium iodide, and the slurry is heated to reflux for 20 hours. The mixture is filtered, and the filtrate is concentrated in vacuo to obtain a crystalline residue. Recrystallization from ethanol gives 16.7 g (67%) of crystals, m.p. 95° C.

Workup

  1. temperaturethe slurry is heated
  2. temperatureto reflux for 20 hours
  3. filtrationThe mixture is filtered
  4. concentrationthe filtrate is concentrated in vacuo
  5. customto obtain a crystalline residue
  6. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-2518d07445f94a539bd1df0123c7de9e
Source dataset
uspto-grants-1989_05
Patent number
US04826990

Reaction notes

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