Dichloromethane → Diethylamino-sulfenyl carbamoyl fluoride

HRID 26950

Reaktionsgleichung

Reaktionsgleichung von HRID 26950
[FH:1].C(Cl)Cl.C[N:6]=[C:7]=[O:8].[CH2:9]([N:11]([CH2:14][CH3:15])[S:12]Cl)[CH3:10]>C(N(CC)CC)C>[CH2:9]([N:11]([CH2:14][CH3:15])[S:12][NH:6][C:7]([F:1])=[O:8])[CH3:10]

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 12228Methyl IsocyanateHCID 14917Hydrofluoric AcidHCID 12297776N,N-diethylaminosulfenyl chloride

Produkt 1

HCID 131711024Diethylamino-sulfenyl carbamoyl fluorideAusbeute 62,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Anhydrous hydrogen fluoride (3.0 g, 0.15 mole) was added to 150 ml of methylene chloride at -10° C. Then 8.6 g of methylisocyanate was added, followed by 20.9 g (0.15 mole) of N,N-diethylaminosulfenyl chloride at 0° C. Triethylamine (15.2 g) was then added at 0° C. over a 15-minute period, and the mixture was stirred at +5° C. for 1 hour. The mixture was then extracted with water (100 ml), saturated sodium bicarbonate solution, and water again. After drying (MgSO4), the solvent was removed in vacuo, and the crude residue was vacuum distilled to give 17 g of N-methyl-N-(diethylamino-sulfenyl carbamoyl fluoride, b.p. 57° C./0.8 mm (62.9 percent yield).

Aufarbeitung

  1. extractionThe mixture was then extracted with water (100 ml), saturated sodium bicarbonate solution, and water again
  2. dry with materialAfter drying (MgSO4)
  3. customthe solvent was removed in vacuo
  4. distillationdistilled

Quellen und Nachweise

ORD-Eintrag
ord-169c72cf116c4a2a91821603167f86f8
Quelldatensatz
uspto-grants-1979_04
Patentnummer
US04151353

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