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

HRID 2239287ノート

反応式

HRID 2239287 の反応式
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]

参加物

5

反応物 2

HCID 6228DimethylformamideHCID 67220372N-(2-(benzyloxy)-4-bromo-6-nitrophenyl)acetamide

生成物 1

HCID 68576258Acetamide, N-[4-cyano-2-nitro-6-(phenylmethoxy)phenyl]-収率 99%

試薬・触媒・溶媒 2

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 178418397HCID 178418397、化合物触媒

反応条件

温度
170 °C

実験手順

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%).

後処理

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

出典と根拠

ORDレコード
ord-9d0b863ace354758aa2c32c4dd3e8132
出典データセット
uspto-grants-2010_05
特許番号
US07723321B2

反応ノート

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