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Methyl morpholine oxide → 5-(2-Chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazoline-7-carbaldehyde

HRID 394097
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인쇄 미리보기

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HRID 394097 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([CH2:18][OH:19])[CH:15]=[C:14]2[C:9]=1[CH2:10][NH:11][C:12](=[O:28])[N:13]2[C:20]1[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:21]=1[Cl:27].C[N+]1([O-])CCOCC1>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([CH:18]=[O:19])[CH:15]=[C:14]2[C:9]=1[CH2:10][NH:11][C:12](=[O:28])[N:13]2[C:20]1[C:21]([Cl:27])=[CH:22][CH:23]=[CH:24][C:25]=1[Cl:26]
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참가 물질

5

반응물 2

HCID 82029Methyl morpholine oxideHCID 226479725-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-7-(hydroxymethyl)-3,4-dihydroquinazolin-2(1H)-one

생성물 1

HCID 226481625-(2-Chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazoline-7-carbaldehyde

시약·촉매·용매 2

HCID 178419074HCID 178419074, 화합물촉매HCID 6344Dichloromethane
용매

실험 절차

To a suspension of 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-7-(hydroxymethyl)-3,4-dihydroquinazolin-2(1H)-one (780 mg, 1.8 mmol) in methylene chloride (15 mL) was added 4-methylmorpholine N-oxide (316 mg, 2.7 mmol). To the resulting clear solution was added molecular sieves (900 mg) followed by tetrapropylammonium perruthenate (32 mg, 0.09 mmol). The resulting mixture was stirred at rt for 2 h. The mixture was then filtered through silica gel eluting with ethyl acetate. Removal of the solvent and subsequent purification by flash chromatography using 25% acetone/hexane provided 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazoline-7-carbaldehyde as a white solid. 1H NMR (CDCl3, 500 MHz): δ 4.43 (abq, 2H, J=15.5 Hz), 5.37 (s, 1H), 6.66 (s, 1H), 7.30-7.60 (m, 8H), 9.85 (s, 1).

후처리

  1. additionTo the resulting clear solution was added molecular sieves (900 mg)
  2. filtrationThe mixture was then filtered through silica gel eluting with ethyl acetate
  3. customRemoval of the solvent and subsequent purification by flash chromatography

출처 및 근거

ORD 기록
ord-f7d75bc3a1634de1bbde02be7fec0261
출처 데이터셋
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06809199B2

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