Ethyl Acetate → HCID 68829816, compound

HRID 747754Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH3:23])=[C:7]([CH:22]=1)[O:8][CH2:9][CH2:10][NH:11][C:12](=[O:21])[C:13]1[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][CH:14]=1)#[N:2].[Br:24]N1C(=O)CCC1=O.C(OCC)(=O)C>C(Cl)(Cl)(Cl)Cl>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:23][Br:24])=[C:7]([CH:22]=1)[O:8][CH2:9][CH2:10][NH:11][C:12](=[O:21])[C:13]1[CH:14]=[CH:15][C:16]([C:19]#[N:20])=[CH:17][CH:18]=1)#[N:2]

Participants

Conditions

Temperature: 100 °C

Procedure

12.0 g (39.3 mmol) of N-[2-(5-cyano-2-methylphenoxy)ethyl]-4-cyanobenzamide was dissolved in 200 ml of carbon tetrachloride. 7.00 g (39.3 mmol) of N-bromosuccinimide and 700 mg (4.26 mmol) of azoisobutyronitrile were added to the solution. After stirring at 100° C. for 3 days, 16.8 g (94.4 mmol) of N-bromosuccinimide and 2.1 g (12.8 mmol) of azoisobutyronitrile were added to the resultant mixture, and they were stirred for additional 2 days. After the treatment with ethyl acetate as the extractant in an ordinary manner, the crude product was obtained, which was purified by the silica gel column chromatography to obtain the title compound.

Workup

stirringwere stirred for additional 2 days
customwhich was purified by the silica gel column chromatography

Sources & evidence

ORD record: ord-c1106eb494db49a2916ea8375930355d
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07396844B1

Reaction notes

Loading…