Oxalyl chloride → 2-(Acetylamino)methyl-5-(3-methoxycarbonylpropionyl)indane

HRID 1077420

Reaktionsgleichung

Reaktionsgleichung von HRID 1077420
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][CH2:3][C:4]([OH:6])=O.C(Cl)(=O)C(Cl)=O.[C:16]([NH:19][CH2:20][CH:21]1[CH2:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22]1)(=[O:18])[CH3:17].[Cl-].[Al+3].[Cl-].[Cl-]>ClC(Cl)C.CN(C)C=O>[C:16]([NH:19][CH2:20][CH:21]1[CH2:29][C:28]2[C:23](=[CH:24][CH:25]=[C:26]([C:4](=[O:6])[CH2:3][CH2:2][C:1]([O:8][CH3:9])=[O:7])[CH:27]=2)[CH2:22]1)(=[O:18])[CH3:17]

Komponenten

7

Edukt 4

HCID 65578Oxalyl chlorideHCID 77487monoMethyl succinateHCID 6451240Aluminum(III) ChlorideHCID 214762872-(Acetylaminomethyl)indane

Produkt 1

HCID 214763072-(Acetylamino)methyl-5-(3-methoxycarbonylpropionyl)indaneAusbeute 93,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 63651,1-DichloroethaneLösungsmittel2×

Versuchsvorschrift

To 48.3 g of methyl hydrogen succinate dissolved in 840 ml of dichloroethane were added 46.4 g of oxalyl chloride and 2 drops of dimethylformamide. The mixture was stirred at room temperature for 5 hours. Then, under ice cooling, 34.6 g of 2-(acetylaminomethyl)indane dissolved in 280 ml of dichloroethane and 97.6 g of anhydrous aluminum chloride were added to the reaction mixture. After the mixture was stirred for 1 hour, the reaction mixture was poured into ice water. The organic layer was collected by separation, washed with water and dried, and the solvent was removed to obtain 51.8 g of 2-(acetylamino) methyl-5-(3methoxycarbonylpropionyl) indane.

Aufarbeitung

  1. stirringAfter the mixture was stirred for 1 hour
  2. customThe organic layer was collected by separation
  3. washwashed with water
  4. customdried
  5. customthe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-10157b5f6f3f4079807535ef4dfd4bd6
Quelldatensatz
uspto-grants-1996_08
Patentnummer
US05543409

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