2-Chloro-6-fluorobenzaldehyde → N-[(E)-(2-chloro-6-fluorophenyl)methylideneamino]-4-iodoaniline

HRID 508714

Reaktionsgleichung

Reaktionsgleichung von HRID 508714
[I:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][NH2:9])=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:12]=1[CH:13]=O>C(O)C>[Cl:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:12]=1/[CH:13]=[N:9]/[NH:8][C:5]1[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=1

Komponenten

4

Edukt 2

HCID 678472-Chloro-6-fluorobenzaldehydeHCID 7045914-Iodophenylhydrazine

Produkt 1

HCID 90020166N-[(E)-(2-chloro-6-fluorophenyl)methylideneamino]-4-iodoanilineAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

To a solution of (4-iodophenyl)hydrazine (1.0 g, 4.27 mmol) in ethanol (10 mL) was slowly added solution of 2-chloro-6-fluorobenzaldehyde (0.675 g, 4.27 mmol) in ethanol (10 mL). The reaction mass was stirred at RT for 5-6 h. The reaction mass was quenched in water and extracted with ethyl acetate. The organic layer was concentrated to afford 1.2 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 6.87 (d, J=8.4 Hz, 2H), 7.26-7.36 (m, 3H), 7.53 (d, J=9.0 Hz, 2H), 8.06 (s, 1H), 10.84 (s, 1H). MS (m/z): 374.87 (M)+.

Aufarbeitung

  1. customThe reaction mass was quenched in water
  2. extractionextracted with ethyl acetate
  3. concentrationThe organic layer was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-ff12325aec0f4b75b80214b3bef7b7f6
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096545B2

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