Sodium Carbonate → 1-(4-Oxo-5-phenyl-3,4-dihydroquinazolin-2-yl)cyclopropanecarbonitrile

HRID 2036832ノート

反応式

HRID 2036832 の反応式
[C:1]([C:3]1([C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:10]=2[C:21]([NH2:23])=[O:22])=O)[CH2:5][CH2:4]1)#[N:2].C([O-])([O-])=O.[Na+].[Na+]>CO>[O:22]=[C:21]1[C:10]2[C:9](=[CH:14][CH:13]=[CH:12][C:11]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:8]=[C:6]([C:3]2([C:1]#[N:2])[CH2:5][CH2:4]2)[NH:23]1

参加物

4

反応物 2

HCID 10340Sodium CarbonateHCID 670558893-(1-Cyanocyclopropanecarboxamido)biphenyl-2-carboxamide

生成物 1

HCID 1363920661-(4-Oxo-5-phenyl-3,4-dihydroquinazolin-2-yl)cyclopropanecarbonitrile収率 113.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
80 °C

実験手順

To a solution 3-(1-cyanocyclopropanecarboxamido)biphenyl-2-carboxamide (0.7 g, 2 mmol) in methanol was added saturated aqueous Na2CO3 (23 mmol) and the reaction mixture stirred at 80° C. for 30 min. The reaction mixture was concentrated under reduced pressure and the resulting residue was diluted with ethyl acetate then washed with water. The organic extracts were dried, concentrated and purified by silica gel chromatography (4% MeOH in DCM) to yield 1-(4-oxo-5-phenyl-3,4-dihydroquinazolin-2-yl)cyclopropanecarbonitrile (0.65 g, 99% yield) as a white solid. LCMS Method T: retention time 1.810 min; [M+1]=288.2.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe resulting residue was diluted with ethyl acetate
  3. washthen washed with water
  4. customThe organic extracts were dried
  5. concentrationconcentrated
  6. custompurified by silica gel chromatography (4% MeOH in DCM)

出典と根拠

ORDレコード
ord-3a1ff1fd1c9744deb44f16ab95fb6fc6
出典データセット
uspto-grants-2013_11
特許番号
US08575184B2

反応ノート

読み込み中…