Methanol → HCID 49872352, Verbindung

HRID 80159

Reaktionsgleichung

Reaktionsgleichung von HRID 80159
[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH2:14][CH2:13][N:12]([C:15]4[CH:16]=[N:17][CH:18]=[CH:19][C:20]=4Cl)[C:11]3=[O:22])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[CH3:23][O-:24].[Na+].CO>O1CCOCC1.C(Cl)(Cl)Cl>[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH2:14][CH2:13][N:12]([C:15]4[CH:16]=[N:17][CH:18]=[CH:19][C:20]=4[O:24][CH3:23])[C:11]3=[O:22])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Komponenten

6

Edukt 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 596362211-Benzothiazol-6-yl-3-(4-chloro-pyridin-3-yl)-imidazolidin-2-one

Produkt 1

HCID 49872352HCID 49872352, VerbindungAusbeute 32,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

1-Benzothiazol-6-yl-3-(4-chloro-pyridin-3-yl)-imidazolidin-2-one (84A: 50 mg, 0.1515 mmol) was added dropwise to a solution of sodium methoxide (0.122 g, 2.259 mmol) in 1,4-dioxane (15 mL) over a period of 5 minutes. The resulting mixture was refluxed for 10 hours. The reaction was monitored by TLC (10% MeOH in CHCl3). The reaction mixture was partitioned between ice water and ethylacetate. The organic layer was dried over Na2SO4 and concentrated. Purification by preparative HPLC afforded 16 mg of the product (31.66% yield).

Aufarbeitung

  1. temperatureThe resulting mixture was refluxed for 10 hours
  2. customThe reaction mixture was partitioned between ice water and ethylacetate
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-d12f0dd3f7b44cb18ce6da01dfe0f625
Quelldatensatz
uspto-grants-2014_09
Patentnummer
USRE045173E1

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