Methyl nitrite → HCID 86759359, Verbindung

HRID 48137

Reaktionsgleichung

Reaktionsgleichung von HRID 48137
[OH-].[Na+].[C:3]([CH2:5][CH:6]=[CH:7][C:8]1[CH:25]=[CH:24][C:11]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([CH:19]=[CH:20][CH2:21][C:22]#[N:23])=[CH:15][CH:14]=2)=[CH:10][CH:9]=1)#[N:4].[N:26]([O:28]C)=O.[N:30]([O-])=[O:31].[Na+]>CO>[C:22]([C:21](=[N:26][OH:28])[CH:20]=[CH:19][C:16]1[CH:15]=[CH:14][C:13]([CH2:12][C:11]2[CH:24]=[CH:25][C:8]([CH:7]=[CH:6][C:5](=[N:30][OH:31])[C:3]#[N:4])=[CH:9][CH:10]=2)=[CH:18][CH:17]=1)#[N:23]

Komponenten

6

Edukt 4

HCID 12231Methyl nitriteHCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 570915964-{4-[4-(3-Cyano-propenyl)-benzyl]-phenyl}-but-3-enenitrile

Produkt 1

HCID 86759359HCID 86759359, VerbindungAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

A solution of sodium hydroxide (0.8 g; 0.02 mol) in 30 ml of methanol is added to a suspension of 4-{4-[4-(3-cyano-propenyl)-benzyl]-phenyl}-but-3-enenitrile (3.0 g; 0.01 mol), prepared as described in example 6.2, in 20 ml of methanol. Methyl nitrite, generated from 2.07 g (0.03 mol) of sodium nitrite as described in example 2.2, is bubbled through the suspension at 2° C. for 25 min, and the mixture is then left at room temperature for 48 h. The solvent is then evaporated, the residue is dissolved in 200 ml of water, extracted with toluene (the extract is discarded), and acidified with conc. hydrochloric acid. The beige precipitate is taken up in ethyl acetate, washed neutral with water, dried (MgSO4) and concentrated by evaporation. 2.7 g (76%) of 4-{4-[4-(3-cyano-3-hydroxyimino-propenyl)-benzyl]-phenyl}-2-hydroxyimino-but-3-enenitrile are obtained as a light brown solid, melting point 142-145° C. (dec).

Aufarbeitung

  1. customprepared
  2. customis bubbled through the suspension at 2° C. for 25 min
  3. customThe solvent is then evaporated
  4. dissolutionthe residue is dissolved in 200 ml of water
  5. extractionextracted with toluene (the extract
  6. washwashed neutral with water
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-696874186176498ab615d634fcfa74ee
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06703182B1

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