But-1-ene-1,3-dione → N-(3-chloro-4-(dihexylamino)phenyl)-3-oxobutanamide

HRID 56198Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=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].[C:22]([CH:25]=[C:26]=[O:27])(=[O:24])[CH3:23]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:26](=[O:27])[CH2:25][C:22](=[O:24])[CH3:23])[CH:5]=[CH:4][C:3]=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]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-chloro-N1,N1-dihexylbenzene-1,4-diamine (3.11 g, 10 mmol) in toluene (50 mL) was added acetyl ketene (1.68 g, 20 mmol) and the mixture was stirred at 80° C. overnight. The mixture was cooled to rt and concentrated in vacuo to give the title compound as blackish oil (3.94 g, 100%).

Workup

temperatureThe mixture was cooled to rt
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-51ab07dd89b54868b4347755c0f77952
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434695B2

Reaction notes

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