Methanol → 5-(2-Methoxy-4-nitrophenyl)oxazole

HRID 1826928Notes

Reaction equation

HRID 1826928 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[C:6]([O:12][CH3:13])[CH:5]=1)([O-:3])=[O:2].CC1C=CC(S([CH2:24][N+:25]#[C-:26])(=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+].CO>O>[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]2[O:9][CH:26]=[N:25][CH:24]=2)=[C:6]([O:12][CH3:13])[CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 27595992-Methoxy-4-nitrobenzaldehyde

Product 1

HCID 101983405-(2-Methoxy-4-nitrophenyl)oxazoleYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 5 L three necked round bottom flask equipped with a condenser and a mechanical stirrer was placed 1B (146.3 g, 0.8076 mol), TOSMIC (157.7 g, 0.8077 mol), K2CO3 (116.6 g, 0.8075 mol) and MeOH (2.5 L). The mixture was heated to reflux under N2 and stirred for 3 hours. Water (1.25 L) was added drop-wise while maintaining the pot temperature between 59–69° C. The resulting slurry was cooled to room temperature, and then to 5° C. with an ice-water bath. After stirring for 30 minutes at 5° C., the slurry was filtered. The resulting cake was washed with water (3×400 mL) and dried in a vacuum oven at 45° C. for 20 hours to give 1C (148.5 g, 84%) as a yellow-reddish solid. 1H NMR (CDCl3) d 8.02 (s, 1H), 7.97 (d, J=2 Hz, 1H), 7.95 (d, J=2 Hz, 1H), 7.86 (s, 1H), 7.78 (s, 1H), 4.11 (s, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux under N2
  3. temperaturewhile maintaining the pot temperature between 59–69° C
  4. customto 5° C.
  5. stirringAfter stirring for 30 minutes at 5° C.
  6. filtrationthe slurry was filtered
  7. washThe resulting cake was washed with water (3×400 mL)
  8. customdried in a vacuum oven at 45° C. for 20 hours

Sources & evidence

ORD record
ord-61a0d299dc5648a6a853c54a36c7c6be
Source dataset
uspto-grants-2006_05
Patent number
US07053111B2

Reaction notes

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