Acrylamide → N-(4-phenoxybutyl)acrylic amide

HRID 1906069

Reaktionsgleichung

Reaktionsgleichung von HRID 1906069
[C:1]([NH2:5])(=[O:4])[CH:2]=[CH2:3].Br[CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-].[K+].C1C2NC3C(=CC=CC=3)SC=2C=CC=1>C1C=CC=CC=1.CN(C)C=O>[O:11]([CH2:10][CH2:9][CH2:8][CH2:7][NH:5][C:1](=[O:4])[CH:2]=[CH2:3])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

7

Edukt 4

HCID 6579Acrylamide2×HCID 7108PhenothiazineHCID 14797Potassium HydroxideHCID 70986(4-Bromobutoxy)benzene

Produkt 1

HCID 13650883N-(4-phenoxybutyl)acrylic amideAusbeute 81,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittel2×HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Added to 20 ml of N,N-dimethylformamide were 1.34 g of acrylic amide and 3.4 g of (4-bromobutoxy)benzene. With stirring, 0.88 g of flaky potassium hydroxide which had been ground in a mortar was added. Phenothiazine was added in an amount of 0.5% based on the acrylic amide. After they were reacted at 0°-5° C. for 6 hours, insoluble matter was filtered off from the liquid reaction mixture. The solvent and unreacted raw materials were distilled off from the filtrate. The residue was extracted with benzene-water, thereby obtaining the intended product in the benzene layer. Benzene was then driven off from the benzene layer to obtain 2.66 g of N-(4-phenoxybutyl)acrylic amide (yield: 81%). It was purified further with column chromatography in which silica gel and benzene were used as an adsorbent and developer respectively. Its melting point was measured and its elementary analysis was also conducted. The following results were obtained. Melting point: 46°-47° C. Elementary analysis data: C, 71.29% (Calculated: 71.19%); H, 7.31% (7.82%); N, 6.15% (6.38%).

Aufarbeitung

  1. additionwas added
  2. customAfter they were reacted at 0°-5° C. for 6 hours
  3. filtrationinsoluble matter was filtered off from the liquid reaction mixture
  4. distillationThe solvent and unreacted raw materials were distilled off from the filtrate
  5. extractionThe residue was extracted with benzene-water
  6. customobtaining the intended product in the benzene layer

Quellen und Nachweise

ORD-Eintrag
ord-71aba9a4503b4bf4900cc95103847716
Quelldatensatz
uspto-grants-1987_03
Patentnummer
US04649219

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