Methanol → 5-(3-Nitrophenyl)oxazole

HRID 254259Notes

Reaction equation

HRID 254259 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[O:8])([O-:3])=[O:2].S([CH2:22][N+:23]#[C-:24])(C1C=CC(C)=CC=1)(=O)=O.CO>COCCOC>[N+:1]([C:4]1[CH:5]=[C:6]([C:7]2[O:8][CH:24]=[N:23][CH:22]=2)[CH:9]=[CH:10][CH:11]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 74493-NitrobenzaldehydeHCID 161915Tosylmethyl isocyanide

Product 1

HCID 27370675-(3-Nitrophenyl)oxazoleYield 100%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

2.04 g (13.5 mmol, 1 eq.) of 3-nitrobenzaldehyde, 2.90 g (14.85 mmol, 1.1 eq.) of tosylmethyl isocyanide, 200 mL of MeOH and 200 mL of DME are introduced into a 1 L flask. 25 g of Amberlyst A26 OH— resin are added and the mixture is heated under reflux for 1 hour. The reaction medium is cooled to room temperature, then the resin is filtered over a frit and rinsed with methanol. After concentration to dryness, 2.56 g (yield=100%) of 5-(3-nitrophenyl)oxazole are obtained. The product is used without subsequent purification.

Workup

  1. addition25 g of Amberlyst A26 OH— resin are added
  2. temperaturethe mixture is heated
  3. temperatureunder reflux for 1 hour
  4. filtrationthe resin is filtered over a frit
  5. washrinsed with methanol

Sources & evidence

ORD record
ord-78368bd22f1d4db79ea183052dc39db9
Source dataset
uspto-grants-2011_01
Patent number
US07875609B2

Reaction notes

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