Water → Benzyl(cyano)methylamine

HRID 974033Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 974033
[CH3:1][N:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([NH2:5])=O.C(N(CC)CC)C.O>C(Cl)(Cl)Cl.[OH-].[Na+]>[CH3:1][N:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]#[N:5]

Komponenten

6

Edukt 3

HCID 962WaterHCID 8471TriethylamineHCID 156760161-benzyl-1-methylurea

Produkt 1

HCID 12526219Benzyl(cyano)methylamineAusbeute 82,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittel2×HCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

To N-methyl-N-benzylurea (1.64 g, 0.01 mol) in chloroform (24 ml) and 50% aqueous sodium hydroxide solution (5.4 ml) was added triethylamine (0.1 g, 0.001 mol) and the mixture was vigorously stirred at room temperature for 3.5 h. After addition of water and chloroform, the mixture was stirred, then extracted with chloroform. The extracts were washed with water, dried with anhydrous sodium sulfate, and evaporated under reduced pressure to a residue, which was chromatographed to afford N-methyl-N-benzylcyanamide (1.2 g, 82% yield) as oily substance: NMR(CDCl3) δ 2.77(s, 3H), 4.14(s, 2H), 7.25-7.50(m, 5H); IR(neat) 2220, 1495, 1455, 1365, 730 cm-1.

Aufarbeitung

  1. stirringthe mixture was stirred
  2. extractionextracted with chloroform
  3. washThe extracts were washed with water
  4. dry with materialdried with anhydrous sodium sulfate
  5. customevaporated under reduced pressure to a residue, which
  6. customwas chromatographed

Quellen und Nachweise

ORD-Eintrag
ord-9d6e5cb53c7b48ffaf1563e5c5b55397
Quelldatensatz
uspto-grants-1991_11
Patentnummer
US05066666

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