Dimethylcarbamoyl Chloride → HCID 21444460, Verbindung

HRID 328232Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 328232
[H-].[Na+].O1CCCC1.[CH3:8][C:9]1[CH:10]=[C:11]([OH:23])[CH:12]=[C:13]([CH3:22])[C:14]=1[S:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1.[CH3:24][N:25]([CH3:29])[C:26](Cl)=[O:27]>O>[CH3:24][N:25]([CH3:29])[C:26](=[O:27])[O:23][C:11]1[CH:12]=[C:13]([CH3:22])[C:14]([S:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[C:9]([CH3:8])[CH:10]=1

Komponenten

6

Edukt 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 8028Tetrahydrofuran3×HCID 24758Sodium hydrideHCID 214444563,5-Dimethyl-4-[(pyridin-2-yl)sulfanyl]phenol

Produkt 1

HCID 21444460HCID 21444460, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a stirred suspension of 240 mg. of sodium hydride in 20 ml. of dry tetrahydrofuran is added a solution of 2.31 g. of 3,5-dimethyl-4-(2-pyridylthio)phenol in 30 ml. of dry tetrahydrofuran. After the effervescence has subsided, a solution of 1.1 g. of N,N-dimethylcarbamoyl chloride in 10 ml. of dry tetrahydrofuran is added dropwise. The reaction mixture is stirred at ambient temperature for 16 hours, and then under reflux for 4 hours. The reaction mixture is cooled to room temperature, and then diluted with an excess of water. The product is extracted into ethyl acetate. The ethyl acetate is washed with water, dried using anhydrous magnesium sulfate, and then evaporated in vacuo to give crude 3,5-dimethyl-4-(2-pyridylthio)phenyl N,N-dimethylcarbamate. The crude product can be purified further by recrystallization.

Aufarbeitung

  1. additionTo a stirred suspension of 240 mg
  2. temperatureunder reflux for 4 hours
  3. temperatureThe reaction mixture is cooled to room temperature
  4. extractionThe product is extracted into ethyl acetate
  5. washThe ethyl acetate is washed with water
  6. customdried
  7. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-39913770e708484b8c8abff61f6646fd
Quelldatensatz
uspto-grants-1977_04
Patentnummer
US04016278

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