Water → 5-Cyano-2-ethoxy-N,4-dimethylbenzamide

HRID 1295923ノート

反応式

HRID 1295923 の反応式
[CH3:1][NH:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8](Br)[C:7]([CH3:11])=[CH:6][C:5]=1[O:12][CH2:13][CH3:14].[C-:16]#[N:17].[Na+].C(OCC)(=O)C.O>C(#N)CC.[Cu](I)I.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>[CH3:1][NH:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([C:16]#[N:17])[C:7]([CH3:11])=[CH:6][C:5]=1[O:12][CH2:13][CH3:14]

参加物

8

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 8929Sodium CyanideHCID 229298455-Bromo-2-ethoxy-N,4-dimethylbenzamide

生成物 1

HCID 229298705-Cyano-2-ethoxy-N,4-dimethylbenzamide収率 58%

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 178418397HCID 178418397、化合物触媒HCID 7854Propionitrile溶媒

実験手順

After dissolving N1,4-dimethyl-5-bromo-2-ethoxybenzamide (200 g) in propionitrile (1.51), sodium cyanide (72 g), copper iodide (14 g) and tetrakis(triphenylphosphine)palladium (42 g) were added under a nitrogen atmosphere and the mixture was heated to reflux for 5 hours. Ethyl acetate and water were added and the reaction mixture was filtered through celite. The precipitated crystals in the filtrate were filtered off (15.4 g). This filtrate was then separated and washed with brine. The organic layer was dried over anhydrous magnesium sulfate and was concentrated after filtering off the insoluble portion. The obtained crystals were filtered off and washed with ethyl acetate (77.64 g). The crystals were combined to yield the title compound (93.04 g) as a white solid.

後処理

  1. additionwere added under a nitrogen atmosphere
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 5 hours
  4. filtrationthe reaction mixture was filtered through celite
  5. filtrationThe precipitated crystals in the filtrate were filtered off (15.4 g)
  6. customThis filtrate was then separated
  7. washwashed with brine
  8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  9. concentrationwas concentrated
  10. filtrationafter filtering off the insoluble portion
  11. filtrationThe obtained crystals were filtered off
  12. washwashed with ethyl acetate (77.64 g)

出典と根拠

ORDレコード
ord-98ee0fdc771c4be2b269a65bdde330ed
出典データセット
uspto-grants-2007_07
特許番号
US07244730B2

反応ノート

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