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Pyridine → 5-Methyl-4-(dimethylaminomethyl)-2-thiophenemethanol N,N,3-trimethyl-3-thiophene carboxamide

HRID 851108
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 851108
[CH3:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([OH:9])=O.[C:10](Cl)(=O)[C:11](Cl)=[O:12].[N:16]1[CH:21]=CC=C[CH:17]=1>C1(C)C=CC=CC=1>[CH3:17][N:16]([CH3:21])[C:7]([C:6]1([CH3:10])[CH:5]=[CH:4][S:3][CH2:2]1)=[O:9].[CH3:1][C:2]1[S:3][C:4]([CH2:11][OH:12])=[CH:5][C:6]=1[CH2:7][N:16]([CH3:21])[CH3:17]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 46254092-Methylthiophene-3-carboxylic acid

Produkt 1

HCID 704178535-Methyl-4-(dimethylaminomethyl)-2-thiophenemethanol N,N,3-trimethyl-3-thiophene carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 2-methyl-3-thiophene carboxylic acid (2 g) and oxalyl chloride (2 ml) in dry toluene (20 ml) was heated under reflux and was treated with pyridine (0.05 ml). The reaction mixture was heated at reflux for 1 h, cooled and partially evaporated. The residue was added to a solution of dimethylamine in toluene at 0° to 5° C. After 2 hours water and diethyl ether were added. The organic phase was washed with dilute hydrochloric acid, sodium hydroxide and water, dried and evaporated to an oil which was distilled to give the title compound (1.4 g) as a colourless oil b.p. 100°/0.1 mm.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux for 1 h
  5. temperaturecooled
  6. custompartially evaporated
  7. additionThe residue was added to a solution of dimethylamine in toluene at 0° to 5° C
  8. additionAfter 2 hours water and diethyl ether were added
  9. washThe organic phase was washed with dilute hydrochloric acid, sodium hydroxide and water
  10. customdried
  11. customevaporated to an oil which
  12. distillationwas distilled

Quellen und Nachweise

ORD-Eintrag
ord-a162273636ee41ea9571ac318e531ee8
Quelldatensatz
uspto-grants-1983_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04382929

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