Pyridine → 4-(4-t-Butylazo-4-cyanopentoxycarbonyl)phthalic Anhydride

HRID 866733

Reaktionsgleichung

Reaktionsgleichung von HRID 866733
Cl[C:2]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[O:10][C:8](=[O:9])[C:7]2=[CH:13][CH:14]=1)=[O:3].[C:15]([N:19]=[N:20][C:21]([C:27]#[N:28])([CH2:23][CH2:24][CH2:25][OH:26])[CH3:22])([CH3:18])([CH3:17])[CH3:16].N1C=CC=CC=1>CCOCC>[C:15]([N:19]=[N:20][C:21]([C:27]#[N:28])([CH3:22])[CH2:23][CH2:24][CH2:25][O:26][C:2]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[O:10][C:8](=[O:9])[C:7]2=[CH:13][CH:14]=1)=[O:3])([CH3:18])([CH3:16])[CH3:17]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 70998Trimellitic anhydride chlorideHCID 233458984-t-Butylazo-4-cyanopentanol

Produkt 1

HCID 543368904-(4-t-Butylazo-4-cyanopentoxycarbonyl)phthalic Anhydride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

To a solution of 2.1 g. (0.01 m) of 4-chloroformylphthalic anhydride in 25 ml ether in a 50 ml 4-neck round bottom flask equipped with a condenser containing a CaCl2 drying tube, a thermometer, a magnetic stirring bar and a dropping funnel was added a solution of 2.0 g. (0.01 m) 2-t-butylazo-2-cyano-5-hydroxypentane (from XIV) and 0.8 g. (0.01 m) pyridine in 10 ml ether. This solution was added dropwise with stirring over 15 minutes holding the temperature between 15° and 22° C with a water bath. The reaction was stirred an additional hour after the addition was completed and the pyridine hydrochloride filtered off. The ether filtrate was dried over anhydrous Na2SO4, filtered and evaporated to dryness leaving 3.1 g. (84%) of a viscous liquid. The infrared spectrum contained 3 carbonyl bands and no OH bands.

Aufarbeitung

  1. additioncontaining a CaCl2 drying tube
  2. additiona thermometer, a magnetic stirring bar and a dropping funnel was added a solution of 2.0 g
  3. additionThis solution was added dropwise
  4. customthe temperature between 15° and 22° C
  5. stirringThe reaction was stirred an additional hour
  6. additionafter the addition
  7. filtrationthe pyridine hydrochloride filtered off
  8. dry with materialThe ether filtrate was dried over anhydrous Na2SO4
  9. filtrationfiltered
  10. customevaporated to dryness
  11. customleaving 3.1 g

Quellen und Nachweise

ORD-Eintrag
ord-0f9f4886c6584476adc3a7e77079ba51
Quelldatensatz
uspto-grants-1978_07
Patentnummer
US04101522

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