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

HRID 56277Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-fluoro-N1,N1-dihexylbenzene-1,4-diamine (2.94 g, 10.0 mmol) in toluene (50 mL) was added acetyl ketene (0.84 g, 10.0 mmol) and the mixture was stirred at 80° C. overnight. The mixture was cooled to rt and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:4) to give the title compound as yellow oil (2.67 g, 70%).

Workup

temperatureThe mixture was cooled to rt
concentrationconcentrated in vacuo
customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:4)

Sources & evidence

ORD record: ord-874a792eff84442a93544f26b183205b
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434695B2

Reaction notes

Loading…