Dichloromethane → 2-cyano-N,N-dihexyl-4-nitroaniline

HRID 56205

Reaction equation

F[C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[C:4]#[N:5].C([O-])([O-])=O.[K+].[K+].[CH2:19]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].C(Cl)Cl>CC#N>[C:4]([C:3]1[CH:6]=[C:7]([N+:10]([O-:12])=[O:11])[CH:8]=[CH:9][C:2]=1[N:25]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])#[N:5]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-fluoro-5-nitrobenzonitrile (1.83 g, 10.0 mmol) in CH3CN (20 mL) were added K2CO3 (2.76 g, 20.0 mmol) and dihexylamine (1.85 g, 9.98 mmol) and the mixture was stirred at 80° C. for 40 h. The mixture was cooled to rt, poured into 100 mL of DCM and washed with water (100 mL×3), brine (100 mL), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=125:2) to give the title compound as yellow oil (2.89 g, 87%).

Workup

temperatureThe mixture was cooled to rt
washwashed with water (100 mL×3), brine (100 mL)
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=125:2)

Sources & evidence

ORD record: ord-df9fc0513de84a9c85d6d8fc5a69e95c
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434695B2

Linked notes

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