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

HRID 1168426Notes

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

Conditions

Temperature: 64 °C

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 N2and 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

temperatureThe mixture was heated
temperatureto reflux under N2and
temperatureThe resulting slurry was cooled to room temperature
customto 5° C.
stirringAfter stirring for 30 minutes at 5° C.
filtrationthe slurry was filtered
washThe resulting cake was washed with water (3×400 mL)
customdried in a vacuum oven at 45° C. for 20 hours

Sources & evidence

ORD record: ord-6f0b60eb3a5a4ec2b4834e6690b296b5
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06624184B1

Reaction notes

Loading…