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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
Notes
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Reaction equation

HRID 394097 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalyst
HCID 6344
Dichloromethane
Solvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-f7d75bc3a1634de1bbde02be7fec0261
Source dataset
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06809199B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes