Triphenylphosphine → 4-Chloro-2-[(3-iodo-1-phenylpropyl)amino]-benzonitrile

HRID 966957Notes

Reaction equation

HRID 966957 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[I-:32].[Li+].[Cl:34][C:35]1[CH:42]=[CH:41][C:38]([C:39]#[N:40])=[C:37]([NH:43][CH:44]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH2:45][CH2:46]O)[CH:36]=1>O1CCCC1>[Cl:34][C:35]1[CH:42]=[CH:41][C:38]([C:39]#[N:40])=[C:37]([NH:43][CH:44]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH2:45][CH2:46][I:32])[CH:36]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 66321Lithium iodideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 222939464-Chloro-2-[(3-hydroxy-1-phenylpropyl)amino]benzonitrile

Product 1

HCID 222939264-Chloro-2-[(3-iodo-1-phenylpropyl)amino]-benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of triphenylphosphine (1.83 g, 6.98 mmol) in dry tetrahydrofuran (30 ml) at 0° C. and under an atmosphere of nitrogen was added diethyl azodicarboxylate (1.2 g, 6.9 mmol) dropwise. After 20 minutes, lithium iodide and 4-chloro-2-[(3-hydroxy-1-phenylpropyl)amino]-benzonitrile (0.8 g, 2.79 mmol) were added to the mixture and stirring was continued for 5 h. The mixture was then concentrated to dryness, and the residue purified on silica (ether/isohexane 1:4). The title compound was isolated as a colourless solid (0.35 g, 32%).

Workup

  1. waitwas continued for 5 h
  2. concentrationThe mixture was then concentrated to dryness
  3. customthe residue purified on silica (ether/isohexane 1:4)

Sources & evidence

ORD record
ord-e024f8768d3a4da2a1042c5c0ab1f6bd
Source dataset
uspto-grants-2005_10
Patent number
US06953797B2

Reaction notes

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