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

HRID 56199Notes

Reaction equation

HRID 56199 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:21][C:22](=[O:27])[CH2:23][C:24](=O)[CH3:25])[CH:5]=[CH:6][C:7]=1[N:8]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[NH3:28]>CO>[NH2:28]/[C:24](/[CH3:25])=[CH:23]\[C:22]([NH:21][C:4]1[CH:5]=[CH:6][C:7]([N:8]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[C:2]([Cl:1])[CH:3]=1)=[O:27]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 90023042N-(3-chloro-4-(dihexylamino)phenyl)-3-oxobutanamide

Product 1

HCID 90022952(Z)-3-amino-N-(3-chloro-4-(dihexylamino)phenyl)but-2-enamideYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of N-(3-chloro-4-(dihexylamino)phenyl)-3-oxobutanamide (3.94 g, 10 mmol), MeOH (50 mL) and ammonia (50 mL) was stirred at rt overnight. The mixture was then concentrated in vacuo to give the title compound as black oil (3.94 g, 100%).

Workup

  1. concentrationThe mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-345c51dcafd5406ab7e822a6f3758b5e
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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