Sulfuric Acid → HCID 16638027, Verbindung

HRID 2293541Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2293541
N[C:2]1[C:3]([O:14][CH3:15])=[CH:4][C:5]([O:12][CH3:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].S(=O)(=O)(O)O.N([O-])=O.[Na+].[C-:25]#[N:26].[Na+]>O>[C:25]([C:2]1[C:3]([O:14][CH3:15])=[CH:4][C:5]([O:12][CH3:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8])#[N:26]

Komponenten

6

Edukt 4

HCID 1118Sulfuric AcidHCID 8929Sodium CyanideHCID 16638096Methyl 5-amino-2,4-dimethoxybenzoateHCID 23668193Sodium Nitrite

Produkt 1

HCID 16638027HCID 16638027, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel5×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A 1.00 g portion of methyl 5-amino-2,4-dimethoxybenzoate was dissolved in 5 ml of water, 0.50 ml of concentrated sulfuric acid was added and then 356 mg of sodium nitrite dissolved in 2 ml of water was added dropwise under ice-cooling, followed by a short period of stirring. Separately, 1.00 g of cuprous cyanide was dissolved in 4 ml of water and, with ice-cooling, 2.00 g of sodium cyanide dissolved in 4 ml of water was added dropwise thereto, followed by 1 hour of stirring. This was mixed with the previously prepared solution and heated at 80° C. to effect the reaction, the resulting reaction solution was mixed with water, extracted with chloroform and dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure and then the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1 to chloroform:methanol=50:1) to give 0.65 g of methyl 5-cyano-2,4-dimethoxybenzoate.

Aufarbeitung

  1. additionwas added dropwise under ice-
  2. temperaturecooling
  3. waitfollowed by a short period
  4. temperaturecooling
  5. additionwas added dropwise
  6. stirringof stirring
  7. additionThis was mixed with the previously prepared solution
  8. customthe reaction
  9. customthe resulting reaction solution
  10. extractionextracted with chloroform
  11. dry with materialdried over anhydrous sodium sulfate
  12. customThe solvent was evaporated under a reduced pressure
  13. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1 to chloroform:methanol=50:1)

Quellen und Nachweise

ORD-Eintrag
ord-16c9f7974842433d9066b9d74aabc2b4
Quelldatensatz
uspto-grants-1997_11
Patentnummer
US05686482

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