Dimethylformamide → methyl 2-{4-[N-methyl-N-(2-benzimidazolyl)amino]phenoxy}propionate

HRID 1446873

Reaktionsgleichung

Reaktionsgleichung von HRID 1446873
[CH3:1][N:2]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)[C:3]1[NH:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.Br[CH:20]([CH3:25])[C:21]([O:23][CH3:24])=[O:22].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:1][N:2]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH:20]([CH3:25])[C:21]([O:23][CH3:24])=[O:22])=[CH:14][CH:13]=1)[C:3]1[NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[N:4]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 95576Methyl 2-bromopropionateHCID 133148184-[N-methyl-N-(2-benzimidazolyl)amino]phenol

Produkt 1

HCID 20553511methyl 2-{4-[N-methyl-N-(2-benzimidazolyl)amino]phenoxy}propionateAusbeute 64,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 4-[N-methyl-N-(2-benzimidazolyl)amino]phenol (1.14 g), methyl 2-bromopropionate (0.80 g), anhydrous potassium carbonate (0.72 g) and dimethylformamide (25 ml) was heated for 4 hours at a temperature of 100° C. with vigorous stirring. After cooling, the mixture was poured into water and the aqueous solution was extracted with dichloromethane. The organic extract was washed with water, dried over anhydrous magnesium sulfate and the solvent was removed by distillation under reduced pressure. The residue was purified by chromatography over silica gel with dichloromethane elution to give methyl 2-{4-[N-methyl-N-(2-benzimidazolyl)amino]phenoxy}propionate (1.0 g) as a colourless oil. The pmr spectrum of the compound was consistent with the assigned structure (CDCl3 ; chemical shift δppm): 1.50, d, 3H; 3.35, s, 3H; 3.70, s, 3H; 4.60, q, 1H; 6.50-7.60, m, 9H.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionthe aqueous solution was extracted with dichloromethane
  3. extractionThe organic extract
  4. washwas washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed by distillation under reduced pressure
  7. customThe residue was purified by chromatography over silica gel with dichloromethane elution

Quellen und Nachweise

ORD-Eintrag
ord-1b968bdda4ef40b1a4f561ab5ca090bc
Quelldatensatz
uspto-grants-1982_02
Patentnummer
US04314065

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