Dimethylformamide → N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(N-benzyloxycarbonyl-p-toluidino)-acetamide

HRID 543741

Reaktionsgleichung

Reaktionsgleichung von HRID 543741
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][C:14](=[O:24])[CH2:15][NH:16][C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.Cl[C:37]([O:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:38]>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][C:14](=[O:24])[CH2:15][N:16]([C:37]([O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[O:38])[C:17]2[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 10042154N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(p-toluidino)acetamide

Produkt 1

HCID 20460509N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(N-benzyloxycarbonyl-p-toluidino)-acetamideAusbeute 84,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A mixture of N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(p-toluidino)acetamide (3.6 g) and anhydrous potassium carbonate (2.5 g) was added to anhydrous dimethylformamide (25 ml). The mixture was vigorously stirred under ice cooling and to the solution was dropwise added over 20 minutes an anhydrous chloroform solution (5 ml) containing benzyl chloroformate (2.04 g). The reaction mixture was poured into ice-water and extracted with chloroform. The extract was washed with water, dried and the solvent was distilled off. The residue was crystallized by treating with ether to give N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(N-benzyloxycarbonyl-p-toluidino)-acetamide (4.3 g), mp 81° to 85° C.

Aufarbeitung

  1. extractionextracted with chloroform
  2. washThe extract was washed with water
  3. customdried
  4. distillationthe solvent was distilled off
  5. customThe residue was crystallized
  6. additionby treating with ether

Quellen und Nachweise

ORD-Eintrag
ord-1160d815c9d64b1188751560b0021423
Quelldatensatz
uspto-grants-1984_05
Patentnummer
US04447436

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