Ethylenediamine → HCID 2990663、化合物

HRID 2041183ノート

反応式

HRID 2041183 の反応式
Br[C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[O:7])=[C:4]([F:17])[CH:3]=1.[Cu](C#N)[C:19]#[N:20].C(N)CN>CN(C=O)C>[C:19]([C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[O:7])=[C:4]([F:17])[CH:3]=1)#[N:20]

参加物

5

反応物 3

HCID 3301EthylenediamineHCID 90711954-Bromo-N-cyclohexyl-2-fluorobenzamideHCID 178418260HCID 178418260、化合物

生成物 1

HCID 2990663HCID 2990663、化合物収率 61%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Heat a mixture of 4-bromo-N-cyclohexyl-2-fluoro-benzamide (1.24 g, 4.13 mmol) and copper cyanide (740 mg, 8.26 mmol) in DMF (20 mL) to reflux for 16 h. Cool the mixture to ambient temperature, add aqueous ethylenediamine and stir for 30 min. Extract the mixture with hexane/EtOAc (1:1), dry the organic layer over Na2SO4, filter and concentrate in vacuo. Purify the residue by chromatography on silica gel eluting with hexane/EtOAc (5:1) to give the desired intermediate as a white solid (620 mg, 61%). MS (ES−) m/z: 245 (M−H)−.

後処理

  1. temperatureHeat
  2. temperatureto reflux for 16 h
  3. extractionExtract the mixture with hexane/EtOAc (1:1)
  4. dry with materialdry the organic layer over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customPurify the residue by chromatography on silica gel eluting with hexane/EtOAc (5:1)

出典と根拠

ORDレコード
ord-d7e636df9bde4dad8c4e8fad74972d92
出典データセット
uspto-grants-2013_11
特許番号
US08580780B2

反応ノート

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