Dimethylformamide → Acetamide, N-[4-cyano-2-nitro-6-(phenylmethoxy)phenyl]-

HRID 2239287Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]([NH:16][C:17](=[O:19])[CH3:18])=[C:4]([N+:20]([O-:22])=[O:21])[CH:3]=1.[CH3:23][N:24](C)C=O>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:23]([C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]([NH:16][C:17](=[O:19])[CH3:18])=[C:4]([N+:20]([O-:22])=[O:21])[CH:3]=1)#[N:24]

Participants

Conditions

Temperature: 170 °C

Procedure

A mixture of N-{4-bromo-2-nitro-6-[(phenylmethyl)oxy]phenyl}acetamide (6.5 g, 17.8 mmol, STEP 1), zinc cyanide (4.18 g, 35.6 mmol), and tetrakis(triphenylphosphine)palladium (2.06 g, 1.78 mmol) in N,N-dimethylformamide (100 mL) was heated to 170° C. for 20 minutes in the microwave synthesizer (Biotage, Emrys Optimizer). After cooling to room temperature, the suspension was filtered, and washed with ethyl acetate. The organic layers were combined, washed with water, dried over magnesium sulfate, and concentrated in vacuum. The residual solid was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (3:1) to afford the title compound as a white solid (5.5 g, 99%).

Workup

temperatureAfter cooling to room temperature
filtrationthe suspension was filtered
washwashed with ethyl acetate
washwashed with water
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuum
customThe residual solid was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (3:1)

Sources & evidence

ORD record: ord-9d0b863ace354758aa2c32c4dd3e8132
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723321B2

Reaction notes

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