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

HRID 843054

Reaction equation

HRID 843054 reaction equation
[Br: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(C)=CC=CC=1.CCOCC>[Br: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 27568393-(3-Bromophenyl)-3-oxopropanenitrile

Product 1

HCID 696866072-(3-Bromobenzoyl)-3-phenylaminoacrylonitrileYield 74.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 7237O-XyleneSolvent

Procedure

A mixture of 2-(3-bromobenzoyl)acetonitrile (16.5 g, 73.6 mmol) and N,N-diphenylformamidine (14.5 g, 73.6 mmol) in xylene (100 ml) was heated at reflux under a nitrogen atmosphere. After 3 h, the reaction mixture was cooled to room temperature and diluted with ether to give 2-(3-bromobenzoyl)-3-phenylaminoacrylonitrile (17.9 g) as a solid.

Workup

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

Sources & evidence

ORD record
ord-4935f7e1780c4aebb72610b5bc2ea39c
Source dataset
uspto-grants-2002_04
Patent number
US06376527B1

Linked notes

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