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p-Toluenesulfonic acid → 2-(4-(4-acetylpiperazin-1-yl)phenyl)quinazolin-4(3H)-one

HRID 591632
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인쇄 미리보기

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HRID 591632 반응식
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[C:11]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=2)[CH2:16][CH2:15]1)(=[O:13])[CH3:12].CC1C=CC(S(O)(=O)=O)=CC=1.OS([O-])=O.[Na+]>CC(N(C)C)=O>[C:11]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:27]=[CH:26][C:23]([C:24]3[NH:6][C:4](=[O:5])[C:3]4[C:2](=[CH:10][CH:9]=[CH:8][CH:7]=4)[N:1]=3)=[CH:22][CH:21]=2)[CH2:16][CH2:15]1)(=[O:13])[CH3:12]
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참가 물질

6

반응물 4

HCID 6101p-Toluenesulfonic acidHCID 6942AnthranilamideHCID 20521464-(4-Acetylpiperazin-1-yl)benzaldehydeHCID 23665763Sodium Bisulfite

생성물 1

HCID 1363480012-(4-(4-acetylpiperazin-1-yl)phenyl)quinazolin-4(3H)-one수율 89%

시약·촉매·용매 1

HCID 31374
Dimethylacetamide
용매

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온도
150 °C

실험 절차

To a mixture of 2-aminobenzamide (1.0 g, 7.35 mmol) and 4-(4-acetylpiperazin-1-yl)benzaldehyde (1.71 g, 7.35 mmol) in DMA (60 mL) was added p-TsOH (0.140 g, 0.73 mmol) and NaHSO3 (0.841 g, 8.1 mmol). The reaction mixture was heated at 150° C. for 21 hours, concentrated to half-volume, diluted with water (300 mL), extracted with CH2Cl2 (2×200 mL), washed with brine (200 mL), dried over anhydrous MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography, eluting with 100% CH2Cl2 to 100% (92:7:1 CHCl3/MeOH/concentrated NH4OH), to afford 2-(4-(4-acetylpiperazin-1-yl)phenyl)quinazolin-4(3H)-one as a yellow solid (2.27 g, 89%).

후처리

  1. concentrationconcentrated to half-volume
  2. additiondiluted with water (300 mL)
  3. extractionextracted with CH2Cl2 (2×200 mL)
  4. washwashed with brine (200 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with 100% CH2Cl2 to 100% (92:7:1 CHCl3/MeOH/concentrated NH4OH)

출처 및 근거

ORD 기록
ord-10d89f78bb49442ea62802f98ed57985
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09238640B2

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