Dimethylformamide → HCID 23076599, compound

HRID 2221523Notes

Reaction equation

HRID 2221523 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)[O:6][C:7]=1[CH3:8].[Br:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[OH:23])[CH:18]=[O:19].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Br:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[O:23][CH2:2][C:3]1[N:4]=[C:5]([C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)[O:6][C:7]=1[CH3:8])[CH:18]=[O:19]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 763083-Bromo-4-hydroxybenzaldehydeHCID 223445824-(Chloromethyl)-2-(furan-2-yl)-5-methyl-1,3-oxazole

Product 1

HCID 23076599HCID 23076599, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-chloromethyl-2-(2-furyl)-5-methyl-1,3-oxazole (4.62 g), 3-bromo-4-hydroxybenzaldehyde (4.28 g), potassium carbonate (2.94 g) and N,N-dimethylformamide (50 mL) was stirred at 90° C. for 4 hrs. Water was poured into the reaction mixture, and the precipitated crystals were collected by filtration to give 3-bromo-4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}benzaldehyde as pale-brown crystals (5.20 g, yield 67%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 146-147° C.

Workup

  1. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-76ff467607c6416e810f193d1f98322f
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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