2-Furancarboxylic acid → HCID 13228917, compound

HRID 1089108Notes

Reaction equation

[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=O.C(N(CC)CC)C.ClC(OCC(C)C)=O.[NH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:32]([CH3:38])[CH2:33][C:34](=[O:37])[NH:35][N:36]=2)=[CH:27][CH:26]=1>ClCCl.CN(C)C=O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:32]([CH3:38])[CH2:33][C:34](=[O:37])[NH:35][N:36]=2)=[CH:27][CH:26]=1)=[O:8]

Participants

Conditions

Temperature: -20 °C

Procedure

In 20 ml of dichloromethane was dissolved 0.56 g (5 m-mol) of 2-furancarboxylic acid. To this solution was added 0.7 ml of triethylamine, and the mixture was cooled to -20° C. Next, 0.65 ml of isobutyl chloroformate was added to the mixture and the whole was stirred for 30 minutes at a temperature from -10° C. to -20° C. To this mixture was added a dimethylformamide solution containing 1.0 g (4.9 m-mol) of 6-(p-aminophenyl)-5-methyl-4,5-dihydropyridazinone. After removing the ice bath, the mixture was stirred for 3 hours at room temperature and the solvent was then distilled off under reduced pressure. Water was added to the residue and a solid material was collected by filtration. The solid material was washed with water and dichloromethane and then recrystallized from methanol-water whereby 570 mg of the title compound was obtained.

Workup

customAfter removing the ice bath
stirringthe mixture was stirred for 3 hours at room temperature
distillationthe solvent was then distilled off under reduced pressure
additionWater was added to the residue
filtrationa solid material was collected by filtration
washThe solid material was washed with water and dichloromethane
customrecrystallized from methanol-water whereby 570 mg of the title compound
customwas obtained

Sources & evidence

ORD record: ord-a64ab6eab3de4a32893f704dcfb703eb
Source dataset: uspto-grants-1990_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04965263

Reaction notes

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