N-bromobutanimide → HCID 68297730、化合物

HRID 919899ノート

反応式

HRID 919899 の反応式
C[O:2][C:3](=O)[CH:4]=[CH:5][C:6](=[C:11]([NH:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=1)[CH3:12])[C:7]([O:9][CH3:10])=[O:8].C[O-].[Na+].[Br:27]N1C(=O)CCC1=O>CO>[CH3:10][O:9][C:7]([C:6]1[CH:5]=[C:4]([Br:27])[C:3](=[O:2])[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=2)[C:11]=1[CH3:12])=[O:8]

参加物

5

反応物 3

HCID 67184N-bromobutanimideHCID 10942334Sodium MethoxideHCID 867141454-[1-(4-Cyano-benzylamino)-ethylidene]-pent-2-enedioic acid dimethyl ester

生成物 1

HCID 68297730HCID 68297730、化合物収率 53%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

MeOH (90 mL) was added to a flask containing 4-[1-(4-cyano-benzylamino)-ethylidene]-pent-2-enedioic acid dimethyl ester (3.35 g, 10.7 mmol). NaOMe solution (2.44 mL, 10.7 mmol, 4.375 M in MeOH) and N-bromosuccinimide (2.28 g, 12.8 mmol) were added, and the resulting mixture was refluxed for 1 h. After cooling to r.t., the solvent was evaporated in vacuo. Saturated NH4Cl (120 mL) was added, and the resulting mixture was extracted with CH2Cl2. The organic layer was dried over MgSO4 and concentrated. The crude product was chromatographed (0-40% EtOAc/hexanes) to give 2.05 g of the title compound. MS: (+) m/z 361.18, 363.14 (M+Na, 79/81Br).

後処理

  1. temperaturethe resulting mixture was refluxed for 1 h
  2. customthe solvent was evaporated in vacuo
  3. additionSaturated NH4Cl (120 mL) was added
  4. extractionthe resulting mixture was extracted with CH2Cl2
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated
  7. customThe crude product was chromatographed (0-40% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-0d3dc784294d44a9ab341530129c8d4d
出典データセット
uspto-grants-2016_03
特許番号
US09271970B2

反応ノート

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