Water → HCID 577823, compound

HRID 908578Notes

Reaction equation

HRID 908578 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=O.C1(N=C=NC2CCCCC2)CCCCC1.O[NH:25][C:26](=[NH:33])[C:27]1[CH:32]=[CH:31][CH:30]=[N:29][CH:28]=1.O>ClCCl>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:8][N:33]=[C:26]([C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)[N:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 69192-Furancarboxylic acidHCID 10868DicyclohexylcarbodiimideHCID 178513339HCID 178513339, compound

Product 1

HCID 577823HCID 577823, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
2.5 °C

Procedure

Furan-2-carboxylic acid (0.8 g; 7 mmol) in 15 ml of dichloromethane was cooled to 0° C., and 0.76 g of 1,3-dicyclohexylcarbodimide (4 mmol) was added slowly. The reaction mixture was stirred at 0-5° C. for 2 hours and filtered. The filtrate was evaporated, the residue was dissolved in 15 ml of pyridine and added 0.43 g of N-hydroxy-nicotinamidine (3.2 mmol). The reaction mixture was heated at reflux until the reaction was finished (measured by TLC), then cooled to room temperature and poured into 100 ml of water. The precipitate was isolated by filtration and dried under vacuum. The product was isolated by column chromatography. Yield 0.23 g (15%). Mp. 110-114° C.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated
  3. dissolutionthe residue was dissolved in 15 ml of pyridine
  4. temperatureThe reaction mixture was heated
  5. temperatureat reflux until the reaction
  6. temperaturecooled to room temperature
  7. customThe precipitate was isolated by filtration
  8. customdried under vacuum
  9. customThe product was isolated by column chromatography

Sources & evidence

ORD record
ord-e3622b2c81cb4befa2f43bc4f021a44f
Source dataset
uspto-grants-2011_09
Patent number
US08017631B2

Reaction notes

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