But-1-ene-1,3-dione → N-(3,5-difluoro-4-morpholinophenyl)-3-oxobutanamide

HRID 56299Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([F:15])[C:8]=1[N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)[NH2:5].[C:16]([CH:19]=[C:20]=[O:21])(=[O:18])[CH3:17]>CCOC(C)=O>[F:15][C:7]1[CH:6]=[C:4]([NH:5][C:20](=[O:21])[CH2:19][C:16](=[O:18])[CH3:17])[CH:3]=[C:2]([F:1])[C:8]=1[N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1

Participants

Conditions

Temperature: 83 °C

Procedure

A mixture of 3,5-difluoro-4-morpholinoaniline (3.42 g, 16.0 mmol) and acetyl ketene (1.61 g, 19.2 mmol) in EtOAc (20 mL) was stirred at 83° 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)=1:1) to give the title compound as a yellow solid (3.10 g, 65%).

Workup

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

Sources & evidence

ORD record: ord-1ee1dd001eb04e0daa06f5dd5364d362
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434695B2

Reaction notes

Loading…