1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-(4-Butylphenyl)-2-furancarboxylic acid 2-(4-hydroxy-3-nitrobenzoyl)hydrazide

HRID 2109419Notes

Reaction equation

HRID 2109419 reaction equation
C1(B(O)O)C=CC=CC=1.C(C1C=CC(B(O)O)=CC=1)CCC.[CH2:23]([C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:37]=[CH:36][O:35][C:34]=2[C:38]([NH:40][NH2:41])=[O:39])=[CH:29][CH:28]=1)[CH2:24][CH2:25][CH3:26].C([O:45][C:46]1[CH:54]=[CH:53][C:49]([C:50](O)=[O:51])=[CH:48][C:47]=1[N+:55]([O-:57])=[O:56])(=O)C.CCN=C=NCCCN(C)C>C(Cl)(Cl)Cl.CN(C=O)C>[OH:45][C:46]1[CH:54]=[CH:53][C:49]([C:50]([NH:41][NH:40][C:38]([C:34]2[O:35][CH:36]=[CH:37][C:33]=2[C:30]2[CH:29]=[CH:28][C:27]([CH2:23][CH2:24][CH2:25][CH3:26])=[CH:32][CH:31]=2)=[O:39])=[O:51])=[CH:48][C:47]=1[N+:55]([O-:57])=[O:56]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 66827Phenylboronic AcidHCID 41008604-Butylphenylboronic acidHCID 140573074-(Acetyloxy)-3-nitrobenzoic acidHCID 688616273-(4-Butylphenyl)-2-furancarboxylic acid hydrazide2×

Product 1

HCID 116332063-(4-Butylphenyl)-2-furancarboxylic acid 2-(4-hydroxy-3-nitrobenzoyl)hydrazide

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

A reaction and treatment was carried out in the same manner as in Reference Example 14 except that the phenylboronic acid used in Reference Example 14 was replaced with 4-butylphenylboronic acid, thereby giving 3-(4-butylphenyl)-2-furancarboxylic acid hydrazide. This 3-(4-butylphenyl)-2-furancarboxylic acid hydrazide (1.62 g), 4-acetoxy-3-nitrobenzoic acid (compound of Reference Example 80, 1.66 g), WSC (1.50 g) and DMF (25 ml) were stirred at 25° C. for 2 hours. The reaction solution was diluted with chloroform and successively washed with water, 20% citric acid solution, aqueous saturated sodium hydrogencarbonate solution and saturated brine. The organic layer was dried over MgSO4, and the solvent was evaporated under reduced pressure. After dissolving the residue in ethanol (15 ml), 2 M aqueous sodium hydroxide solution (16 ml) was added at 25° C. and stirred for 2 hours. The reaction solution was neutralized with hydrochloric acid solution and extracted with ethyl acetate. The organic layer was dried over MgSO4, and the solvent was evaporated under reduced pressure. The residue was recrystallized from acetonitrile, thereby giving 1.80 g of the desired compound.

Workup

  1. customA reaction and treatment
  2. washsuccessively washed with water, 20% citric acid solution, aqueous saturated sodium hydrogencarbonate solution and saturated brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. customthe solvent was evaporated under reduced pressure
  5. dissolutionAfter dissolving the residue in ethanol (15 ml)
  6. addition2 M aqueous sodium hydroxide solution (16 ml) was added at 25° C.
  7. extractionextracted with ethyl acetate
  8. dry with materialThe organic layer was dried over MgSO4
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-05fdde788c974580906212459020db12
Source dataset
uspto-grants-2009_04
Patent number
US07514452B2

Reaction notes

Loading…