Dimethylamine → N-(2-tert-butyl-5-nitrophenyl)-2-(dimethylamino)acetamide

HRID 502724Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 502724
Br[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:7]=1[C:15]([CH3:18])([CH3:17])[CH3:16])=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH3:25][NH:26][CH3:27]>C1COCC1>[C:15]([C:7]1[CH:8]=[CH:9][C:10]([N+:12]([O-:14])=[O:13])=[CH:11][C:6]=1[NH:5][C:3](=[O:4])[CH2:2][N:26]([CH3:27])[CH3:25])([CH3:18])([CH3:17])[CH3:16]

Komponenten

5

Edukt 3

HCID 674DimethylamineHCID 11430Potassium CarbonateHCID 219613852-bromo-N-(2-tert-butyl-5-nitrophenyl)acetamide

Produkt 1

HCID 21961377N-(2-tert-butyl-5-nitrophenyl)-2-(dimethylamino)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2-Bromo-N-(2-tert-butyl-5-nitrophenyl)acetamide (80 g, 253, mmol) and potassium carbonate (70 g, 506 mmol) were combined in THF (1.75 L), and the mixture was cooled to 0° C. N,N-Dimethylamine (40 ml of a 2 M solution in THF, 800 mmol) was then added to the mixture through an addition funnel over a 30-minute period. The mixture was then stirred at room temperature for 16 hours. The mixture was then filtered and the filtrate was concentrated. The crude material was purified by silica chromatography using 50% EtOAc:hexanes as the eluent to give N-(2-tert-butyl-5-nitrophenyl)-2-(dimethylamino)acetamide as a brown solid.

Aufarbeitung

  1. filtrationThe mixture was then filtered
  2. concentrationthe filtrate was concentrated
  3. customThe crude material was purified by silica chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1da5c2ebd7d74b2895748df0605e485a
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776869B2

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