Cyanogen Bromide → HCID 10375434, compound

HRID 744743Notes

Reaction equation

HRID 744743 reaction equation
[N:1]#CBr.[CH2:4]([N:6]([C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1)[CH2:7]C)[CH3:5]>CCOCC>[CH2:4]([N:6]([C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1)[C:7]#[N:1])[CH3:5]

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 66547N,N-Diethyl-alpha-naphthylamine

Product 1

HCID 10375434HCID 10375434, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of cyanogen bromide (3.32 g, 31.3 mmol) and N,N-diethyl-1-naphthylamine (5 g, 25 mmol) was heated at 100° C. for 4 hours under nitrogen. It was then allowed to cool to room temperature, ether was added, and the insoluble N,N-diethyl-1-naphthylamine hydrobromide was filtered off. The ether layer was washed with 15% aqueous HCl solution (2×50 ml), water (2×50 ml), and dried over MgSO4. It was filtered, concentrated and the residue was flash chromatographed on silica gel to give N-ethyl-N-(1-naphthyl)-cyanamide (2.34 g, 48%) as a yellow thick liquid.

Workup

  1. temperatureto cool to room temperature
  2. filtrationthe insoluble N,N-diethyl-1-naphthylamine hydrobromide was filtered off
  3. washThe ether layer was washed with 15% aqueous HCl solution (2×50 ml), water (2×50 ml)
  4. dry with materialdried over MgSO4
  5. filtrationIt was filtered
  6. concentrationconcentrated
  7. customchromatographed on silica gel

Sources & evidence

ORD record
ord-fa7a698903e5427babca5cea870be9b2
Source dataset
uspto-grants-1996_09
Patent number
US05559154

Reaction notes

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