Nitric Acid → 1-Acetamido-2-nitro-3,5-bis(trifluoromethyl)benzene

HRID 53805

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1-acetamido-3,5-bis(trifluoromethyl)benzene (400 mg, 1.37 mmol) in concentrated H2SO4 (3 mL) at 0° C. was added dropwise 70% HNO3 (0.4 mL, Baker). The mixture was stirred at 0° C. for 0.5 h, then at room temperature for 3 h and it was poured into ice water (10 g). The precipitate was collected by filtration, affording 400 mg of crude product which contained two compounds by 1H NMR. It was separated on a column of silica gel, eluted with chloroform, to afford 134 mg of pure 1-acetamido-2-nitro-3,5-bis(trifluoromethyl)benzene as white long needles. mp: 190°-2° C., 1H NMR (CDCl3): δ 2.226 (s, 3H), 7.765 (s, 1H), 7.978 (s, 1H); 8.918 (s, 1H).

Workup

waitat room temperature for 3 h
filtrationThe precipitate was collected by filtration
customaffording 400 mg of crude product which
customIt was separated on a column of silica gel
washeluted with chloroform

Sources & evidence

ORD record: ord-0efd3ef062964cf0acdd2fd1226f93bf
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05620979

Linked notes

Loading…