Glycine → 2-(5,6-dichloro-1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)acetic acid

HRID 571242Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 571242
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[C:7](=[O:12])O[C:5]2=[O:13].[NH2:14][CH2:15][C:16]([OH:18])=[O:17]>C1(C)C(C)=CC=CC=1>[Cl:11][C:10]1[CH:9]=[C:8]2[C:4](=[CH:3][C:2]=1[Cl:1])[C:5](=[O:13])[N:14]([CH2:15][C:16]([OH:18])=[O:17])[C:7]2=[O:12]

Komponenten

4

Edukt 2

HCID 750GlycineHCID 703344,5-Dichlorophthalic anhydride

Produkt 1

HCID 7123142-(5,6-dichloro-1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)acetic acidAusbeute 92,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

To a solution of 5,6-dichloroisobenzofuran-1,3-dione (2 g, 9.22 mmol) in xylene (10 ml), 2-aminoacetic acid (0.761 g, 10.14 mmol) was added, and the reaction was heated at 160° C. for 40 hours. The precipitate that formed during the reaction was filtered, washed with water and hexanes and dried affording 2-(5,6-dichloro-1,3-dioxoisoindolin-2-yl)acetic acid (2.33 g, 8.50 mmol, 92% yield).

Aufarbeitung

  1. customThe precipitate that formed during the reaction
  2. filtrationwas filtered
  3. washwashed with water and hexanes
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-f09dff56da224d8f93e27bc479d718c2
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09024027B2

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