Methanimidamide, N,N-diphenyl- → 2-(3-Iodobenzoyl)-3-phenylaminoacrylonitrile

HRID 429379

Reaction equation

HRID 429379 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([CH2:7][C:8]#[N:9])=[O:6].[C:13]1([N:19](C2C=CC=CC=2)[CH:20]=N)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1(C)C=CC=CC=1.CCOCC>[I:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([C:7](=[CH:20][NH:19][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:8]#[N:9])=[O:6]

Participants

5

Reactant 2

HCID 78296Methanimidamide, N,N-diphenyl-HCID 116231793-Iodobenzoylacetonitrile

Product 1

HCID 670242742-(3-Iodobenzoyl)-3-phenylaminoacrylonitrileYield 62.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-(3-iodobenzoyl)acetonitrile (36.2 g, 133.5 mmol) and N,N-diphenylformamidine (26.2 g, 133.5 mmol) in toluene (200 ml) was heated at reflux under a nitrogen atmosphere. After 8 h, the reaction mixture was cooled to room temperature and diluted with ether (200 ml) to give 2-(3-iodobenzoyl)-3-phenylaminoacrylonitrile (31.2 g) as a solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under a nitrogen atmosphere

Sources & evidence

ORD record
ord-011e87efc5f549d19e59f703074df519
Source dataset
uspto-grants-2001_11
Patent number
US06316466B1

Linked notes

Loading…