Tetrahydro-2,5-dimethoxyfuran-3-carbaldehyde → N-[6-(3-Formyl-pyrrol-1-yl)-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-methanesulfonamide

HRID 2069199Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2069199
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[NH:8][C:7](=[O:15])[N:6]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[C:5]2=[O:21].C[O:23][CH:24]1[CH:28]([CH:29]=O)[CH2:27][CH:26](OC)O1>C(O)(=O)C.C(OCC)(=O)C>[CH:24]([C:28]1[CH:27]=[CH:26][N:1]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][C:11]=2[N+:12]([O-:14])=[O:13])[NH:8][C:7](=[O:15])[N:6]([NH:16][S:17]([CH3:20])(=[O:18])=[O:19])[C:5]3=[O:21])[CH:29]=1)=[O:23]

Komponenten

5

Edukt 2

HCID 567310Tetrahydro-2,5-dimethoxyfuran-3-carbaldehydeHCID 11674068N-(6-Amino-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide

Produkt 1

HCID 11574709N-[6-(3-Formyl-pyrrol-1-yl)-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-methanesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of N-(6-amino-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide (470 mg, 1.49 mmol) and 2,5-dimethoxytetrahydrofuran-3-aldehyde (796 mg, 4.47 mmol) in acetic acid (0.5 ml) is refluxed for five hours. The solvent is removed by rotavapor evaporation to give a brown oil which is dissolved in ethyl acetate and washed three times with water. The organic layer is dried over magnesium sulfate, filtered and the solvent removed by rotavapor evaporation to give the title compound nearly pure as a brown solid, m.p. 230-245° C. (decomp).

Aufarbeitung

  1. customThe solvent is removed by rotavapor evaporation
  2. customto give a brown oil which
  3. washwashed three times with water
  4. dry with materialThe organic layer is dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent removed by rotavapor evaporation

Quellen und Nachweise

ORD-Eintrag
ord-230093f861a84476abfde61b1ac46a30
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299085B2

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