Nitrogen → HCID 19756482, compound

HRID 1587768Notes

Reaction equation

HRID 1587768 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1.[C:11]1([C:17]#[CH:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N#N>C(N(CC)CC)C.[Cu]I>[C:11]1([C:17]#[C:18][C:2]2[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 947NitrogenHCID 10821PhenylacetyleneHCID 11776TriphenylphosphineHCID 27914Benzeneacetonitrile, 4-bromo-

Product 1

HCID 19756482HCID 19756482, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8471TriethylamineSolvent

Procedure

A mixture of 49 g (0.25 mol) 4-bromobenzylcyanide, 30 g (0.3 mol) phenylacetylene, 0.1 g di(triphenylphosphine)-palladium(II-dichloride, 0.1 g copper(I)iodide and 0.2 g triphenylphosphine in 300 ml triethylamine are heated for 20 hours under a blanket of N2 and vigorously stirred. The mixture is then evaporated under water jet vacuum, the residue heated in hexane and the undissolved solid sucked off and dried. The thus obtained title compound is employed as such in the following reaction step.

Workup

  1. customThe mixture is then evaporated under water jet vacuum
  2. temperaturethe residue heated in hexane
  3. customdried

Sources & evidence

ORD record
ord-d4160843bea84963b1a63c3965335e50
Source dataset
uspto-grants-1993_06
Patent number
US05219876

Reaction notes

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