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Hydrochloric Acid → Ethyl 2-chlorobenzyl[4-cyano-2-nitro-6-(trifluoromethyl)phenyl]carbamate

HRID 495632
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 495632
Br[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([N:12]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])[C:13](=[O:17])[O:14][CH2:15][CH3:16])=[C:4]([N+:26]([O-:28])=[O:27])[CH:3]=1.Cl.[CH3:30][N:31](C)C=O>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][N:12]([C:5]1[C:6]([C:8]([F:11])([F:10])[F:9])=[CH:7][C:2]([C:30]#[N:31])=[CH:3][C:4]=1[N+:26]([O-:28])=[O:27])[C:13](=[O:17])[O:14][CH2:15][CH3:16]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 22327381Ethyl 4-bromo-2-nitro-6-(trifluoromethyl)phenyl(2-chlorobenzyl)carbamate

Produkt 1

HCID 69744412Ethyl 2-chlorobenzyl[4-cyano-2-nitro-6-(trifluoromethyl)phenyl]carbamateAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11186
Zinc cyanide (Zn(CN)2)
Katalysator
HCID 178418397HCID 178418397, VerbindungKatalysator

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Ethyl 4-bromo-2-nitro-6-(trifluoromethyl)phenyl(2-chlorobenzyl)carbamate (620.3 mg) was dissolved in N,N-dimethylformamide (30 ml), and to the solution were added zinc cyanide (302.4 mg) and tetrakis(triphenylphosphine)palladium(0) (1.116 g). The mixture was heated at 60° C. and stirred for 7 hours. After allowing to cool, to the reaction mixture was added 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The resultant residue was purified by silica gel column (100 g, hexane:ethyl acetate=3:1) to give the title compound (322.6 mg, 59%).

Aufarbeitung

  1. temperatureto cool, to the reaction mixture
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resultant residue was purified by silica gel column (100 g, hexane:ethyl acetate=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-d4498674f1fa409bba71912b1bf7b4ed
Quelldatensatz
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06939887B2

Notizen zur Reaktion

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