Dimethylcarbamoyl Chloride → N,N-Dimethyl-N'-(2-dimethylaminoethyl)-N'-(4,6-dimethyl-2-pyridyl)urea Dihydrochloride

HRID 1395528Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1395528
[CH3:1][N:2]([CH3:14])[CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([CH3:13])[N:7]=1.C(N(CC)CC)C.[CH3:22][N:23]([CH3:27])[C:24]([Cl:26])=[O:25]>C1C=CC=CC=1>[ClH:26].[ClH:26].[CH3:22][N:23]([CH3:27])[C:24]([N:5]([CH2:4][CH2:3][N:2]([CH3:14])[CH3:1])[C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([CH3:13])[N:7]=1)=[O:25]

Komponenten

5

Edukt 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 128576222-(2-Dimethylaminoethylamino)-4,6-dimethylpyridine

Produkt 1

HCID 12857640N,N-Dimethyl-N'-(2-dimethylaminoethyl)-N'-(4,6-dimethyl-2-pyridyl)urea DihydrochlorideAusbeute 144,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

2-(2-Dimethylaminoethylamino)-4,6-dimethylpyridine (7.73 g, 0.04 mole) and triethylamine (4.8 g, 0.048 mole) are dissolved in 200 ml of anhydrous benzene. Dimethyl carbamoyl chloride (4.85 g, 0.045 mole) is added, the mixture stirred at room temperature for 2 hours and then refluxed four hours. After cooling and dilution with 200 ml of diethyl ether, the triethylamine hydrochloride is filtered off and the filtrate concentrated under vacuum. For purification the crude product is taken up in 200 ml diethyl ether and filtered thru Super-Cel. On addition of ethanolic hydrogen chloride to the filtrate, the product crystallizes and is filtered off to obtain 11 g of solid, m.p. 204°. Recrystallization from 150 ml ethanol and 250 ml diethyl ether yields 10.29 g, m.p. 205°-206° C. (d).

Aufarbeitung

  1. temperaturerefluxed four hours
  2. temperatureAfter cooling
  3. filtrationdilution with 200 ml of diethyl ether, the triethylamine hydrochloride is filtered off
  4. concentrationthe filtrate concentrated under vacuum
  5. customFor purification the crude product
  6. filtrationfiltered
  7. additionOn addition of ethanolic hydrogen chloride to the filtrate
  8. customthe product crystallizes
  9. filtrationis filtered off

Quellen und Nachweise

ORD-Eintrag
ord-427bab30ae7540f1a8bafa8c6b47b734
Quelldatensatz
uspto-grants-1980_05
Patentnummer
US04203988

Notizen zur Reaktion

Wird geladen…