Chlorosuccinimide → (1E)-N-hydroxy-4-phenylmethoxybenzenecarboximidoyl chloride

HRID 75842

Reaktionsgleichung

Reaktionsgleichung von HRID 75842
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12](/[CH:13]=[N:14]\[OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:18]N1C(=O)CCC1=O>>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12](/[C:13](/[Cl:18])=[N:14]\[OH:15])=[CH:16][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

3

Edukt 2

HCID 31398ChlorosuccinimideHCID 5403280(Z)-4-(benzyloxy)benzaldehyde oxime

Produkt 1

HCID 10901405(1E)-N-hydroxy-4-phenylmethoxybenzenecarboximidoyl chloride

Versuchsvorschrift

To (Z)-4-(benzyloxy)benzaldehyde oxime (11.3 g) in N,N′-Dimethyl formamide (57 ml), N-Chlorosuccinimide (7.98 g) was added and the reaction mixture was stirred for 3 hours and then solvent was evaporated to dark brown residue. To this residue water was added and extracted with Ethyl acetate. Organic layer was collected and dried over Na2SO4 and concentrated to obtain pale brown solid, which was crystallized from DCM-Petroleum ether to obtain the title compound as white solid. Yield: 7.9 g (60%); 1HNMR (DMSO-d6; 300 MHz): δ 12.17 (s, 1H), 7.73 (d, 2H), 7.33-7.47 (m, 5H), 7.11 (d, 2H) 5.16 (s, 2H).

Aufarbeitung

  1. customsolvent was evaporated to dark brown residue
  2. additionTo this residue water was added
  3. extractionextracted with Ethyl acetate
  4. customOrganic layer was collected
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto obtain pale brown solid, which
  8. customwas crystallized from DCM-Petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-0ef6adba63234c178b2ce0821706cf56
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835428B2

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