Octylamine → N-Octyl-3-(2-Nitrophenyl)propenamide

HRID 848567

Reaktionsgleichung

Reaktionsgleichung von HRID 848567
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]=[CH:11][C:12]([OH:14])=O)([O-:3])=[O:2].C(N(CC)CC)C.ClC(OCC)=O.[CH2:28]([NH2:36])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]>ClCCl>[CH2:28]([NH:36][C:12](=[O:14])[CH:11]=[CH:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]

Komponenten

6

Edukt 4

HCID 8143OctylamineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 928203-(2-Nitrophenyl)acrylic acid

Produkt 1

HCID 54507938N-Octyl-3-(2-Nitrophenyl)propenamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

A mixture of 9.7 g. of 3-(2-nitrophenyl)propenoic acid, 5.6 g. of triethylamine and 240 ml. of dichloromethane was stirred at room temperature for 20 minutes, and then it was cooled in an ice-bath. To the mixture was then added, dropwise, during 15 minutes, a solution of 6.0 g. of ethyl chloroformate in 20 ml. of dichloromethane. After 15 minutes of stirring, a solution of 7.1 g. of octylamine in 20 ml. of dichloromethane was added dropwise, during 10 minutes. The reaction mixture was allowed to warm to room temperature, and then it was washed successively with 1 N potassium carbonate, 1 N hydrochloric acid, water and saturated sodium chloride. The resulting solution was dried and evaporated in vacuo, leaving 14.5 g. (95%) yield of the title compound as a tan solid.

Aufarbeitung

  1. additionA mixture of 9.7 g
  2. temperatureit was cooled in an ice-bath
  3. additionTo the mixture was then added
  4. washit was washed successively with 1 N potassium carbonate, 1 N hydrochloric acid, water and saturated sodium chloride
  5. customThe resulting solution was dried
  6. customevaporated in vacuo
  7. customleaving 14.5 g

Quellen und Nachweise

ORD-Eintrag
ord-b8b4f755a1de45b4853e028a8fe4176d
Quelldatensatz
uspto-grants-1981_10
Patentnummer
US04296129

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