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Cyanuric chloride → Methyl 4-[(4,5-diisopropylfuran-2-carbonyl)amino]benzoate

HRID 1023704
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1023704
[CH:1]([C:4]1[CH:5]=[C:6]([C:12]([OH:14])=O)[O:7][C:8]=1[CH:9]([CH3:11])[CH3:10])([CH3:3])[CH3:2].N1C(Cl)=NC(Cl)=NC=1Cl.C(N(CC)CC)C.[NH2:31][C:32]1[CH:41]=[CH:40][C:35]([C:36]([O:38][CH3:39])=[O:37])=[CH:34][CH:33]=1>CC(C)=O.CN(C)C1C=CN=CC=1>[CH:1]([C:4]1[CH:5]=[C:6]([C:12]([NH:31][C:32]2[CH:33]=[CH:34][C:35]([C:36]([O:38][CH3:39])=[O:37])=[CH:40][CH:41]=2)=[O:14])[O:7][C:8]=1[CH:9]([CH3:10])[CH3:11])([CH3:2])[CH3:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 7954Cyanuric chlorideHCID 8471TriethylamineHCID 12082Methyl 4-aminobenzoateHCID 584205144,5-Diisopropylfuran-2-carboxylic acid

Produkt 1

HCID 67395533Methyl 4-[(4,5-diisopropylfuran-2-carbonyl)amino]benzoateAusbeute 89,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14284
4-(Dimethylamino)pyridine
Katalysator
HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A solution of 4,5-diisopropylfuran-2-carboxylic acid (50 mg, 0.255 mmol) and cyanuric chloride (71 mg, 0.385 mmol) in acetone (3 ml) was added with triethylamine (142 μl, 1.021 mmol), and the mixture was stirred at room temperature for 3.5 hours. The reaction mixture was added with methyl 4-aminobenzoate (77 mg, 0.510 mmol), and the mixture was further stirred for 14 hours. The reaction solvent was evaporated, then the residue was dissolved in pyridine (1 ml), the solution was added with 4-dimethylaminopyridine (1 mg, 8.20 μmol), and the mixture was stirred at room temperature for 4 hours. Pyridine was evaporated, and then the reaction mixture was dissolved in 10% methanol-chloroform, the solution was added with silica gel (1.0 g), and the mixture was evaporated to dryness. The residue was purified by silica gel chromatography [hexane-ethyl acetate (6:1)] to obtain methyl 4-[(4,5-diisopropylfuran-2-carbonyl)amino]benzoate (75 mg, 89%) as colorless prisms.

Aufarbeitung

  1. stirringthe mixture was further stirred for 14 hours
  2. customThe reaction solvent was evaporated
  3. dissolutionthe residue was dissolved in pyridine (1 ml)
  4. stirringthe mixture was stirred at room temperature for 4 hours
  5. customPyridine was evaporated
  6. dissolutionthe reaction mixture was dissolved in 10% methanol-chloroform
  7. additionthe solution was added with silica gel (1.0 g)
  8. customthe mixture was evaporated to dryness
  9. customThe residue was purified by silica gel chromatography [hexane-ethyl acetate (6:1)]

Quellen und Nachweise

ORD-Eintrag
ord-a939961a1e2345c4ad57a37bd8d47e01
Quelldatensatz
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08722730B2

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