Ammonia → N-(2-methoxy-5-thioureidophenylmethyl)carbamic acid t-butyl ester

HRID 1861923Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1861923
[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][C:9]1[CH:14]=[C:13]([NH2:15])[CH:12]=[CH:11][C:10]=1[O:16][CH3:17])([CH3:4])([CH3:3])[CH3:2].[NH3:19].[C:20](Cl)(Cl)=[S:21]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][C:9]1[CH:14]=[C:13]([NH:15][C:20]([NH2:19])=[S:21])[CH:12]=[CH:11][C:10]=1[O:16][CH3:17])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 222AmmoniaHCID 10040ThiophosgeneHCID 22981333Tert-butyl 5-amino-2-methoxybenzylcarbamate

Produkt 1

HCID 22981237N-(2-methoxy-5-thioureidophenylmethyl)carbamic acid t-butyl esterAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of the compound (52 mg) obtained in Example 119 and N,N-dimethylaminopyridine (53 mg) in methylene chloride (5 ml), thiophosgene (0.02 ml) was added dropwise and stirred at room temperature for 15 min. To the reaction mixture, 28% aqueous ammonia solution (5 ml) was added and stirred at room temperature for 1.5 h. After neutralization with 2 N HCl, the reaction mixture was extracted with methylene chloride and the organic layer was washed successively with water and a saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent, ethyl acetate) to give 58 mg of the titled compound (yield, 91%).

Aufarbeitung

  1. additionwas added dropwise
  2. stirringstirred at room temperature for 1.5 h
  3. extractionAfter neutralization with 2 N HCl, the reaction mixture was extracted with methylene chloride
  4. washthe organic layer was washed successively with water
  5. dry with materiala saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (eluent, ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-29dbac057db04e5fb7c184b539250a78
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06534546B1

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