Water → N-[(4-Methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2,2-dimethyl-1,3-benzodioxole-4-sulfonamide

HRID 542682Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 542682
[CH3:1][C:2]1([CH3:15])[O:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([S:11]([NH2:14])(=[O:13])=[O:12])[C:4]=2[O:3]1.C[Al](C)C.[CH3:20][O:21][C:22]1[CH:27]=[C:26]([CH3:28])[N:25]=[C:24]([NH:29][C:30](=O)[O:31]C)[N:23]=1.O>C(Cl)Cl.Cl.C(O)(=O)C>[CH3:20][O:21][C:22]1[CH:27]=[C:26]([CH3:28])[N:25]=[C:24]([NH:29][C:30]([NH:14][S:11]([C:10]2[C:4]3[O:3][C:2]([CH3:15])([CH3:1])[O:6][C:5]=3[CH:7]=[CH:8][CH:9]=2)(=[O:13])=[O:12])=[O:31])[N:23]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 13072161Methyl (4-methoxy-6-methylpyrimidin-2-yl)carbamateHCID 134554192,2-Dimethyl-1,3-benzodioxole-4-sulfonamideHCID 16682925Trimethylaluminum

Produkt 1

HCID 13455420N-[(4-Methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2,2-dimethyl-1,3-benzodioxole-4-sulfonamideAusbeute 26,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidKatalysatorHCID 176Acetic AcidLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 0.55 g 2,2-dimethyl-1,3-benzodioxole-4-sulfonamide, prepared in Example 1, in 30 ml methylene chloride at ambient temperature under nitrogen was added 1.2 ml of trimethylaluminum (2M in toluene). After stirring 15 minutes at ambient temperature, 0.47 g of methyl [4-methoxy-6-methylpyrimidin-2-yl]carbamate, prepared according to the procedure of Example 3, was added and the reaction mixture was heated at reflux 16 hours. The reaction mixture was cooled to ambient temperature and 75 ml H2O, 10 ml glacial acetic acid, and 10 drops hydrochloric acid were sequentially added. The organic phase was separated, dried, and the solvent removed under reduced pressure to give an oil. Crystallization of the oil from a mixture of butyl chloride, hexane and ether gave 0.25 g white solid, m.p. 180°-183° C. The infrared spectrum showed a carbonyl absorption at 1705 cm-1 indicative of the title compound.

Aufarbeitung

  1. additionwas added
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux 16 hours
  4. temperatureThe reaction mixture was cooled to ambient temperature
  5. customThe organic phase was separated
  6. customdried
  7. customthe solvent removed under reduced pressure
  8. customto give an oil
  9. customCrystallization of the oil
  10. additionfrom a mixture of butyl chloride, hexane and ether

Quellen und Nachweise

ORD-Eintrag
ord-dbb04166cd7245c69c7b87103f79fbde
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04659368

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