Toluene → 2-Amino-5-chloro-N-(5-chloropyridin-2-yl)benzamide

HRID 12124

Reaktionsgleichung

Reaktionsgleichung von HRID 12124
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].C1(C)C=CC=CC=1.[Cl:26][C:27]1[CH:38]=[C:31]2[C:32](OC(=O)[NH:36][C:30]2=[CH:29][CH:28]=1)=[O:33]>O1CCCC1>[NH2:36][C:30]1[CH:29]=[CH:28][C:27]([Cl:26])=[CH:38][C:31]=1[C:32]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1)=[O:33]

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 661742-Amino-5-chloropyridineHCID 784805-Chloroisatoic anhydrideHCID 3251421Potassium bis(trimethylsilyl)amide

Produkt 1

HCID 219064182-Amino-5-chloro-N-(5-chloropyridin-2-yl)benzamideAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 2-amino-5-chloropyridine (328 mg, 2.55 mmol) in tetrahydrofuran (5 ml) was 0.5M potassium bis(trimethylsilyl)amide in toluene (10 ml, 5.05 mmol) dropwise at −78° C. After stirred for additional 0.5 hr at −78° C., the mixture was added 5-chloroisatoic anhydride (0.5 g, 2.55 mmol) at −78° C. The mixture was warmed up to r.t gradually and stirred overnight. After quenched by saturated ammonium chloride solution, the mixture was extracted by ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated to give (2-amino-5-chlorophenyl)-N-(5-chloro(2-pyridyl))carboxamide (0.71 g, 100%). MS found for C12H9Cl2N3O M+=282, (M+2)+=284.

Aufarbeitung

  1. customdropwise at −78° C
  2. temperatureThe mixture was warmed up
  3. stirringstirred overnight
  4. customAfter quenched by saturated ammonium chloride solution
  5. extractionthe mixture was extracted by ethyl acetate
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8d1da3bc63a34c6499333c394caf4bb7
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727982B2

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