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Triethylamine → Methyl 2,6-Bis(trifluoromethyl)-4-(diphenylaminocarbonyloxy)-3-pyridinecarboxylate

HRID 395399
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 395399
[F:1][C:2]([F:19])([F:18])[C:3]1[C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([OH:13])[CH:6]=[C:5]([C:14]([F:17])([F:16])[F:15])[N:4]=1.C(N(CC)CC)C.[C:27]1([N:33]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:34](Cl)=[O:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(#N)C>[F:19][C:2]([F:18])([F:1])[C:3]1[C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([O:13][C:34]([N:33]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:35])[CH:6]=[C:5]([C:14]([F:17])([F:16])[F:15])[N:4]=1
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Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 65741N,N-Diphenylcarbamic chlorideHCID 178498966Methyl 2,6-bis(trifluoromethyl)-4-hydroxy-3-pyridinecarboxylate

Produkt 1

HCID 22668835Methyl 2,6-Bis(trifluoromethyl)-4-(diphenylaminocarbonyloxy)-3-pyridinecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel
2×

Versuchsvorschrift

To a solution of 2 g (0.0069 mol) of methyl 2,6-bis(trifluoromethyl)-4-hydroxy-3-pyridinecarboxylate (example 4 of U.S. Pat. No. 4,655,816) in 20 mL of acetonitrile was added 0.7 g of triethylamine. A solution of 1.6 g (0.0069 mol) of diphenylcarbamyl chloride in 20 mL of acetonitrile was added to the above mixture and the resulting mixture was stirred at room temperature over the weekend. The precipitate formed was filtered off and the filtrate was concentrated in vacuo. The residue was slurried with ether. The insoluble material was filtered. The ether filtrate was concentrated and the residue was recrystallized from cyclohexane to give a white solid, mp 114-116° C.

Aufarbeitung

  1. customThe precipitate formed
  2. filtrationwas filtered off
  3. concentrationthe filtrate was concentrated in vacuo
  4. filtrationThe insoluble material was filtered
  5. concentrationThe ether filtrate was concentrated
  6. customthe residue was recrystallized from cyclohexane
  7. customto give a white solid, mp 114-116° C.

Quellen und Nachweise

ORD-Eintrag
ord-feecd162de734566bdda605c841419d9
Quelldatensatz
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06605624B1

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