Acetonitrile → HCID 19757983, compound

HRID 1587373Notes

Reaction equation

HRID 1587373 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[C:7]([N:9]=[N+:10]=[N-:11])=[O:8])([O-:3])=[O:2].[C:15](#[N:17])[CH3:16]>>[N+:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[C:7]([N:9]1[CH:4]=[C:5]([C:6]23[CH2:7][N:17]([CH2:13][CH2:12]2)[CH2:15][CH2:16]3)[N:11]=[N:10]1)=[O:8])([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 137973m-Nitrobenzoyl azide

Product 1

HCID 19757983HCID 19757983, compound

Procedure

A solution of 4-(triphenylphosphinemethylenecarbonyl)-1-azabicyclo [2.2.1]heptane (D24) (4 g, 0.01 mole) in dry acetonitrile (80 ml) was treated with m-nitrobenzoylazide* (3.8 g, 0.020 mole) under nitrogen and the solution heated to reflux for 2 h. The solution was then concentrated in vacuo to a gum which was dissolved in ethyl acetate (30 ml) and allowed to stand at 0° C. overnight when the title compound (D25) (1.35 g, 0.0043 mole, 43%) crystallised out.

Workup

  1. temperaturethe solution heated
  2. temperatureto reflux for 2 h
  3. concentrationThe solution was then concentrated in vacuo to a gum which
  4. dissolutionwas dissolved in ethyl acetate (30 ml)

Sources & evidence

ORD record
ord-7e00562350234382af4867177b499678
Source dataset
uspto-grants-1993_06
Patent number
US05217975

Reaction notes

Loading…