Ethyl chloroformate → N-(1-Methyldecyl)-3-(3-Nitrophenyl)-2-butenamide

HRID 66810Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 66810
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]([CH3:15])=[CH:11][C:12]([OH:14])=O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].ClC(OCC)=O.[CH3:22][CH:23]([NH2:33])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>ClCCl.C(N(CC)CC)C>[CH3:22][CH:23]([NH:33][C:12](=[O:14])[CH:11]=[C:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[CH3:15])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Komponenten

6

Edukt 3

HCID 10928Ethyl chloroformateHCID 1144762-UndecanamineHCID 544021563-(3-Nitrophenyl)-2-butenoic acid

Produkt 1

HCID 53905448N-(1-Methyldecyl)-3-(3-Nitrophenyl)-2-butenamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel4×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a stirred slurry of 5.2 g. of the 3-(3-nitrophenyl)-2-butenoic acid from Preparation 12 having a melting point of 208°-210° C., in 100 ml. of dichloromethane, was added 2.8 g. of triethylamine in 10 ml. of dichloromethane. This was followed by the addition of a solution of 3.0 g. of ethyl chloroformate in 20 ml. of dichloromethane, during 20 minutes. Stirring was continued for 30 minutes, and then a solution of 1-methyldecylamine in 20 ml. of dichloromethane was added dropwise during 25 minutes. Stirring was continued overnight, and the the reaction mixture was washed successively with 1 N potassium carbonate, water and saturated sodium chloride. The resulting solution was dried using sodium sulfate, and then it was evaporated in vacuo leaving an oil which solidified on trituration under petroleum ether. This afforded 4.9 g. of the title compound, m.p. 72.5°-74° C.

Aufarbeitung

  1. additionThis was followed by the addition of a solution of 3.0 g
  2. stirringStirring
  3. waitwas continued overnight
  4. washthe the reaction mixture was washed successively with 1 N potassium carbonate, water and saturated sodium chloride
  5. customThe resulting solution was dried
  6. customit was evaporated in vacuo
  7. customleaving an oil which

Quellen und Nachweise

ORD-Eintrag
ord-921caf7094484586aeaa6606fc5056d7
Quelldatensatz
uspto-grants-1982_08
Patentnummer
US04343813

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