Hydrochloric Acid → HCID 53770272, Verbindung

HRID 1598907Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1598907
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:22])[CH2:10][NH:11][C:12]([NH:14][C:15]1[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=1)=[O:13].[I-].[K+].[C:25]([O:29][C:30](=[O:33])[CH2:31]Br)([CH3:28])([CH3:27])[CH3:26].C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.O>[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([CH2:31][C:30]([O:29][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:33])[C:9](=[O:22])[CH2:10][NH:11][C:12]([NH:14][C:15]1[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=1)=[O:13]

Komponenten

10

Edukt 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 18930549HCID 18930549, Verbindung

Produkt 1

HCID 53770272HCID 53770272, VerbindungAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of N-(2-iodophenyl)-2-(3-m-tolylureido)acetamide (1.02 g, 2.5 mmol) in DMSO (5 ml) are added at room temperature potassium iodide (83 mg, 0.2 mmol), tetra-n-butylammonium bromide (81 mg, 0.1 mmol), t-butylbromoacetate (0.55 ml, 3.75 mmol) and potassium carbonate (1.04 g, 7.5 mmol), and stirred at room temperature for 2.25 hours. To the reaction mixture are added water and ethyl acetate, and the pH is adjusted to 2 with 2N hydrochloric acid. The aqueous layer is extracted twice with ethyl acetate. The organic layer is washed with 0.1N hydrochloric acid, water and saturated saline, dried over anhydrous magnesium sulfate, and then concentrated. To the residue is added isopropylether, and the precipitated solid is filtered off to obtain the objective compound (1.20 g). Yield 92%.

Aufarbeitung

  1. extractionThe aqueous layer is extracted twice with ethyl acetate
  2. washThe organic layer is washed with 0.1N hydrochloric acid, water and saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. additionTo the residue is added isopropylether
  6. filtrationthe precipitated solid is filtered off

Quellen und Nachweise

ORD-Eintrag
ord-7bda12a7c0fc4d3d93900e4523bc204e
Quelldatensatz
uspto-grants-1998_04
Patentnummer
US05739162

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