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Triethylamine → ethyl 2-chloro-N-[[[3,5-dichloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]benzenecarboximidate

HRID 2198429
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Reaktionsgleichung

Reaktionsgleichung von HRID 2198429
[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4](=[NH:8])[O:5][CH2:6][CH3:7].[Cl:13][C:14]1[CH:15]=[C:16]([N:31]=[C:32]=[O:33])[CH:17]=[C:18]([Cl:30])[C:19]=1[O:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=1.C(N(CC)CC)C>CC(C)=O>[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4](=[N:8][C:32]([NH:31][C:16]1[CH:17]=[C:18]([Cl:30])[C:19]([O:20][C:21]2[CH:22]=[CH:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=2)=[C:14]([Cl:13])[CH:15]=1)=[O:33])[O:5][CH2:6][CH3:7]
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Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 13092607Ethyl 2-chlorobenzimidateHCID 130926093,5-Dichloro-4-(4-nitrophenoxy)phenylisocyanate

Produkt 1

HCID 53641175ethyl 2-chloro-N-[[[3,5-dichloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]benzenecarboximidate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of ethyl 2-chlorobenzimidate hydrofluoroborate (1.90 g., 7.00 mmol), 3,5-dichloro-4-(4-nitrophenoxy)phenylisocyanate (2.28 g., 7.00 mmol) and triethylamine (0.72 g., 7.20 mmol) in acetone (20 ml) is stirred at room temperature for four hours under an atmosphere of dry nitrogen. The reaction mixture is concentrated under reduced pressure and the residue partitioned between ethyl acetate and water. The organic phase is washed sequentially with dilute hydrochloric acid, dilute sodium bicarbonate, and brine. After drying over sodium sulfate, the ethyl acetate solution is concentrated under reduced pressure and the residue chromatographed over silica gel eluting with 20% ethyl acetate in hexane. The product fractions are combined and concentrated under reduced pressure to leave the title compound as an amorphous solid.

Aufarbeitung

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customthe residue partitioned between ethyl acetate and water
  3. washThe organic phase is washed sequentially with dilute hydrochloric acid, dilute sodium bicarbonate, and brine
  4. dry with materialAfter drying over sodium sulfate
  5. concentrationthe ethyl acetate solution is concentrated under reduced pressure
  6. customthe residue chromatographed over silica gel eluting with 20% ethyl acetate in hexane
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4600534be54849d1900df576fc0a4526
Quelldatensatz
uspto-grants-1982_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04357347

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