Pyridine → N-butyl-N-(3-hydroxymethylphenyl)-bromoacetamide

HRID 1275998

Reaktionsgleichung

Reaktionsgleichung von HRID 1275998
[CH2:1]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][OH:13])[CH:7]=1)[CH2:2][CH2:3][CH3:4].N1C=CC=CC=1.[Br:20][CH2:21][C:22](Br)=[O:23].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[CH2:1]([N:5]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][OH:13])[CH:7]=1)[C:22](=[O:23])[CH2:21][Br:20])[CH2:2][CH2:3][CH3:4]

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 11430Potassium CarbonateHCID 61147Bromoacetyl bromideHCID 22322603[3-(Butylamino)phenyl]methanol

Produkt 1

HCID 22323007N-butyl-N-(3-hydroxymethylphenyl)-bromoacetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 3.42 g (19.2 mmol) of the compound of Example 532A in 20 ml toluene, was added 2.42 ml (30 mmol) pyridine. The mixture was cooled to 0° C.; 4.025 gm (20.0 mmol) of bromoacetyl bromide (diluted with 5 ml toluene) was added in a dropwise fashion. The reaction mixture was allowed to stir for 5 hours at 0° C. and then was allowed to warm to room temperature. Saturated potassium carbonate solution was added, and the mixture was stirred vigorously for 2 hours. The mixture was extracted with EtOAc; the organic layer was washed with 1N H3PO4, water, and brine.

Aufarbeitung

  1. temperatureto warm to room temperature
  2. stirringthe mixture was stirred vigorously for 2 hours
  3. extractionThe mixture was extracted with EtOAc
  4. washthe organic layer was washed with 1N H3PO4, water, and brine

Quellen und Nachweise

ORD-Eintrag
ord-a12f475ab6d6437bb1d940f32dd67f4f
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06162927

Verknüpfte Notizen

Wird geladen…