But-1-ene-1,3-dione → HCID 90023598, compound

HRID 56207Notes

Reaction equation

HRID 56207 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([NH2:9])[CH:6]=[CH:5][C:4]=1[N:10]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])#[N:2].[C:23]([CH:26]=[C:27]=[O:28])(=[O:25])[CH3:24]>CCOC(C)=O>[C:1]([C:3]1[CH:8]=[C:7]([NH:9][C:27](=[O:28])[CH2:26][C:23](=[O:25])[CH3:24])[CH:6]=[CH:5][C:4]=1[N:10]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])#[N:2]

Participants

4

Reactant 2

HCID 12642904But-1-ene-1,3-dioneHCID 1179660632-cyano-N1,N1-dihexylbenzene-1,4-diamine

Product 1

HCID 90023598HCID 90023598, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-cyano-N1,N1-dihexylbenzene-1,4-diamine (1.55 g, 5.14 mmol) in EtOAc (30 mL) was added acetyl ketene (0.52 g, 6.19 mmol) with stirring and the mixture was stirred at 80° C. overnight. The mixture was then cooled to rt and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1) to give the title compound as yellow oil (1.47 g, 74%).

Workup

  1. stirringthe mixture was stirred at 80° C. overnight
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1)

Sources & evidence

ORD record
ord-25402cda647e4775ab1e3a992dc054ff
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

Loading…