Ammonia → (Z)-3-amino-N-(3-cyano-4-(dihexylamino)phenyl)but-2-enamide

HRID 56208Notes

Reaction equation

HRID 56208 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:22][C:23](=[O:28])[CH2:24][C:25](=O)[CH3:26])[CH:6]=[CH:7][C:8]=1[N:9]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])#[N:2].[NH3:29]>CO>[NH2:29]/[C:25](/[CH3:26])=[CH:24]\[C:23]([NH:22][C:5]1[CH:6]=[CH:7][C:8]([N:9]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[C:3]([C:1]#[N:2])[CH:4]=1)=[O:28]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 90023598N-(3-cyano-4-(dihexylamino)phenyl)-3-oxobutanamide

Product 1

HCID 90022969(Z)-3-amino-N-(3-cyano-4-(dihexylamino)phenyl)but-2-enamideYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of N-(3-cyano-4-(dihexylamino)phenyl)-3-oxobutanamide (1.47 g, 3.81 mmol), MeOH (15 mL) and ammonia (15 mL) was stirred at rt overnight. The mixture was concentrated in vacuo to give the title compound as black oil (1.30 g, 88%).

Workup

  1. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-af8d51602c5843c0afb91c84da09b43c
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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