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

HRID 489846

Reaction equation

HRID 489846 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[C:7]([CH2:9][C:10]#[N:11])=[O:8])([O-:3])=[O:2].[C:15]1([N:21](C2C=CC=CC=2)[CH:22]=N)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1(C)C(C)=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[C:7]([C:9](=[CH:22][NH:21][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:10]#[N:11])=[O:8])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 78296Methanimidamide, N,N-diphenyl-HCID 123827443-(3-Nitrophenyl)-3-oxopropanenitrile

Product 1

HCID 696860762-(3-Nitrobenzoyl)-3-phenylaminoacrylonitrileYield 74%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 2-(3-nitrobenzoyl)acetonitrile (13.75 g, 72.3 mmol) and N,N-diphenylformamidine (14.2 g, 72.3 mmol) in xylene (200 ml) was heated at reflux under nitrogen atmosphere. After 3 h, the reaction mixture was cooled to room temperature and diluted with xylenes to give 2-(3-nitrobenzoyl)-3-phenylaminoacrylonitrile (15.7 g) as a yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen atmosphere

Sources & evidence

ORD record
ord-93ab486cf8a142eeaea8b1bd8ea2aa6b
Source dataset
uspto-grants-2005_12
Patent number
US06979693B2

Linked notes

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