Potassium Phosphate, Tribasic → 1-Benzothiazol-6-yl-4-methyl-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

HRID 2383915

Reaktionsgleichung

Reaktionsgleichung von HRID 2383915
[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH:14](C(F)(F)F)[CH2:13][NH:12][C:11]3=[O:19])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.I[C:21]1[CH:22]=[N:23][CH:24]=[CH:25][C:26]=1[CH3:27].[CH3:28]NC1CCCCC1NC.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.C(OCC)(=O)C.O1CCOCC1>[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH2:14][CH:13]([CH3:28])[N:12]([C:21]4[CH:22]=[N:23][CH:24]=[CH:25][C:26]=4[CH3:27])[C:11]3=[O:19])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Komponenten

8

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 5510741-N,2-N-dimethylcyclohexane-1,2-diamineHCID 144235133-Iodo-4-methylpyridineHCID 596362031-Benzothiazol-6-yl-5-trifluoromethyl-imidazolidin-2-one

Produkt 1

HCID 498719611-Benzothiazol-6-yl-4-methyl-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-oneAusbeute 1.541,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83717Copper iodideKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Using the same reaction conditions and work up as described in Example 1, step-3,1-benzothiazol-6-yl-5-trifluoromethyl-imidazolidin-2-one (I-172b: 0.15 g, 0.0005 mol) was refluxed with 3-Iodo-4-methyl-pyridine (0.168 g, 0.0007 mol), copper iodide (0.01 g, 0.00005 mol), N,N′-Dimethyl-cyclohexane-1,2-diamine (0.01 g, 0.000015 mol), potassium phosphate (0.3 g, 0.001 mol) and 1,4-dioxane (20 mL) at 120° C. for 12 hours to afford the crude product. The reaction was monitored by TLC (100% ethyl acetate). Purification by column chromatography on silica gel (2% methanol in DCM) afforded 75 mg of the product (39.47% yield).

Aufarbeitung

  1. customthe same reaction conditions
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (2% methanol in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-a872f2258bf646b594ff81b6db45ca82
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263635B2

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