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Diazald → Methyl o-(1-hydroxy-4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)benzoate

HRID 973364
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 973364
[OH-].[K+].[CH3:3]C1C=CC(S(N(N=O)C)(=O)=O)=CC=1.[N+](=C)=[N-].[OH:20][N:21]1[C:25](=[O:26])[C:24]([CH:28]([CH3:30])[CH3:29])([CH3:27])[N:23]=[C:22]1[C:31]1[CH:39]=[CH:38][CH:37]=[CH:36][C:32]=1[C:33]([OH:35])=[O:34]>C(OCC)(=O)C.C(O)C.CCOCC>[OH:20][N:21]1[C:25](=[O:26])[C:24]([CH:28]([CH3:30])[CH3:29])([CH3:27])[N:23]=[C:22]1[C:31]1[CH:39]=[CH:38][CH:37]=[CH:36][C:32]=1[C:33]([O:35][CH3:3])=[O:34]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 6628Diazald2×HCID 9550DiazomethaneHCID 14797Potassium HydroxideHCID 15029348o-(1-Hydroxy-4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)benzoic acid

Produkt 1

HCID 15029352Methyl o-(1-hydroxy-4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)benzoateAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittel2×HCID 3283Diethyl EtherLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of potassium hydroxide (0.19 g, 0.00339 mol) and ethanol is added portionwise to a 0° C. mixture of Diazald® N-methyl-N-nitroso-p-toluenesulfonamide (0.73 g, 0.0034 mol) and ether. The mixture is kept in an ice-bath for 10 minutes then in an water bath for 10 minutes. The diazomethane is distilled into a mixture of o-(1-hydroxy-4-isopropyl-4-methyl-5-oxo-2-imi-dazolin-2-yl)benzoic acid (0.67 g, 0.00243 mol) and ethanol. After 45 minutes the reaction mixture is quenched with acetic acid and concentrated in vacuo to give an oil. The oil is dissolved into ethyl acetate, dried over anhydrous magnesium sulfate and concentrated in vacuo to yield an off-white solid. The solid is chromatographed using silica gel and methylene chloride/ethyl acetate 3:1 as eluent to give the title compound as a white solid (0.18 g, 26%), mp 146°-150° C., identified by IR and NMR spectral analyses.

Aufarbeitung

  1. waitin an water bath for 10 minutes
  2. customAfter 45 minutes the reaction mixture is quenched with acetic acid
  3. concentrationconcentrated in vacuo
  4. customto give an oil
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto yield an off-white solid
  8. customThe solid is chromatographed

Quellen und Nachweise

ORD-Eintrag
ord-ccccce07ac934270a6cb5b1eb987a777
Quelldatensatz
uspto-grants-1991_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05062881

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