Hydroxyamine hydrochloride → 1-(2,6-Dichlorophenyl)-5-(2-chlorophenyl)-7-(1-hydroxyiminocyclohexan-4-yl)-3,4-dihydro-2(1H)-quinazolinone

HRID 394090Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 394090
Cl.[NH2:2][OH:3].[C:4]([O-:7])(O)=O.[Na+].[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[C:11]=1[N:17]1[C:26]2[C:21](=[C:22]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[Cl:40])[CH:23]=[C:24]([CH:27]3[CH2:32][CH2:31][C:30](=O)[CH2:29][CH2:28]3)[CH:25]=2)[CH2:20][NH:19]C1=O>CO>[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[C:11]=1[N:17]1[C:26]2[C:21](=[C:22]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[Cl:40])[CH:23]=[C:24]([CH:27]3[CH2:32][CH2:31][C:30](=[N:2][OH:3])[CH2:29][CH2:28]3)[CH:25]=2)[CH2:20][NH:19][C:4]1=[O:7]

Komponenten

5

Edukt 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 226480091-(2,6-Dichlorophenyl)-5-(2-chlorophenyl)-7-(1-cyclohexanon-4-yl)-3,4-dihydro-2(1H)-quinazolinone2×

Produkt 1

HCID 226481531-(2,6-Dichlorophenyl)-5-(2-chlorophenyl)-7-(1-hydroxyiminocyclohexan-4-yl)-3,4-dihydro-2(1H)-quinazolinone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of hydroxylamine hydrochloride (29 mg, 0.416 mmol) in methanol (1.0 mL) was added solid NaHCO3 (37 mg, 0.437 mmol). After stirring 15 minutes at RT 1-(2,6-Dichlorophenyl)-5-(2-chlorophenyl)-7-(1-cyclohexanon-4-yl)-3,4-dihydro-2(1H)-quinazolinone (52 mg, 0.104 mmol) (INTERMEDIATE 73) was added. After stirring 18 hours the solution was concentrated. The residue was suspended in DCM and the solid filtered. The filtrate solution was concentrated and the residue purified by preparative thin layer chromatography using 5% MeOH in DCM as the eluent to give 1-(2,6-Dichlorophenyl)-5-(2-chlorophenyl)-7-(1-hydroxyiminocyclohexan-4-yl)-3,4-dihydro-2(1H)-quinazolinone. 1H NMR (CDCl3, 500 MHz): selected data 1.53 (m, 2H), 1.87 (dt, 1H, J=5.4, 14.2 Hz), 1.98 (m, 2H), 2.19 (m, 1H), 2.57 (brd, 1H, J=14.4 Hz), 2.64 (m, 1H), 3.38 (brd, 1H, J=15.2 Hz).

Aufarbeitung

  1. additionwas added
  2. concentrationwas concentrated
  3. filtrationthe solid filtered
  4. concentrationThe filtrate solution was concentrated
  5. customthe residue purified by preparative thin layer chromatography

Quellen und Nachweise

ORD-Eintrag
ord-70e333731d734a9d97b4dda8c4631195
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06809199B2

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