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

HRID 2036832노트

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HRID 2036832 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

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온도
80 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-3a1ff1fd1c9744deb44f16ab95fb6fc6
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575184B2

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