2-Furancarboxylic acid → HCID 13228917, compound

HRID 980819Notes

Reaction equation

HRID 980819 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

7

Reactant 4

HCID 69192-Furancarboxylic acidHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 161928Ici 109,081

Product 1

HCID 13228917HCID 13228917, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

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. M.P. 213°-216° C.

Workup

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

Sources & evidence

ORD record
ord-3510174d12914f1db30feee5a76e220e
Source dataset
uspto-grants-1987_01
Patent number
US04639451

Reaction notes

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