Dimethylformamide → HCID 23076605, compound

HRID 2221545Notes

Reaction equation

HRID 2221545 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].C(=O)([O-])[O-].[K+].[K+].[CH:20]([C:22]1[CH:23]=[CH:24][C:25]([OH:32])=[C:26]([CH:31]=1)[C:27]([O:29][CH3:30])=[O:28])=[O:21].CN(C)C=O>O>[CH:20]([C:22]1[CH:23]=[CH:24][C:25]([O:32][CH2:2][C:3]2[N:4]=[C:5]([C:9]3[O:10][CH:11]=[CH:12][CH:13]=3)[O:6][C:7]=2[CH3:8])=[C:26]([CH:31]=1)[C:27]([O:29][CH3:30])=[O:28])=[O:21]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 14363598Methyl 5-FormylsalicylateHCID 223445824-(Chloromethyl)-2-(furan-2-yl)-5-methyl-1,3-oxazole

Product 1

HCID 23076605HCID 23076605, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-chloromethyl-2-(2-furyl)-5-methyl-1,3-oxazole (7.13 g), potassium carbonate (3.84 g), methyl 5-formyl-2-hydroxybenzoate (5.0 g) and N,N-dimethylformamide (100 mL) was stirred at 90° C. for 15 hrs. Water was poured into the reaction mixture, and the precipitated crystals were collected by filtration to give methyl 5-formyl-2-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}benzoate as pale-brown crystals (8.67 g, 91%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 121-122° C.

Workup

  1. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-adcdadc550824a218ba88f9f2839d395
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

Loading…