Triethylamine → cinnamyl-N-methyl-3,4,5-trimethoxyphenylpropiolamide

HRID 597587

Reaktionsgleichung

Reaktionsgleichung von HRID 597587
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]#[C:14][C:15]([OH:17])=O)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].C(N(CC)CC)C.ClC(OCC)=O.[CH3:31][NH:32][CH2:33][CH:34]=[CH:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>O1CCCC1.C(OCC)C.C(Cl)Cl>[CH2:33]([N:32]([CH3:31])[C:15](=[O:17])[C:14]#[C:13][C:5]1[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)[CH:34]=[CH:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 189183N-methyl-3-phenylprop-2-en-1-amineHCID 125218533-(3,4,5-Trimethoxyphenyl)prop-2-ynoic acid

Produkt 1

HCID 54089509cinnamyl-N-methyl-3,4,5-trimethoxyphenylpropiolamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittel3×HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To the solution of 11.8 g of 3,4,5-trimethoxyphenylpropiolic acid in 50 ml of tetrahydrofuran, 7.1 g of triethylamine are added while stirring, followed by 50 ml of diethyl ether. The mixture is cooled with ice and to the resulting suspension the solution of 5.4 g of ethyl chloroformate in 25 ml of diethyl ether is added during 5 minutes. The mixture is stirred for 15 minutes at 0°-5°, whereupon the solution of 7.35 g of N-methylcinnamylamine in 35 ml of diethyl ether is added dropwise, followed by 80 ml of methylene chloride. The mixture is stirred for 30 minutes and allowed to warm to room temperature. It is washed with N hydrochloric acid, N aqueous sodium hydroxide and saturated aqueous sodium chloride, dried and evaporated under reduced pressure, to yield the N cinnamyl-N-methyl- 3,4,5-trimethoxyphenylpropiolamide.

Aufarbeitung

  1. additionis added during 5 minutes
  2. additionis added dropwise
  3. stirringThe mixture is stirred for 30 minutes
  4. washIt is washed with N hydrochloric acid, N aqueous sodium hydroxide and saturated aqueous sodium chloride
  5. customdried
  6. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-77fbe492bb3a46448b1d12af98489f01
Quelldatensatz
uspto-grants-1977_03
Patentnummer
US04014899

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