Sodium hydride → 3-{2-[2-(4-tert-Butyl-phenyl)-thiazol-4-ylmethoxy]-ethyl}-phenyl amine

HRID 585173

Reaktionsgleichung

Reaktionsgleichung von HRID 585173
[H-].[Na+].[OH:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([NH2:12])[CH:9]=[CH:10][CH:11]=1.Cl[CH2:14][C:15]1[N:16]=[C:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:22][CH:21]=2)[S:18][CH:19]=1>C1OCCOCCOCCOCCOC1.C1COCC1>[C:26]([C:23]1[CH:22]=[CH:21][C:20]([C:17]2[S:18][CH:19]=[C:15]([CH2:14][O:3][CH2:4][CH2:5][C:6]3[CH:7]=[C:8]([NH2:12])[CH:9]=[CH:10][CH:11]=3)[N:16]=2)=[CH:25][CH:24]=1)([CH3:29])([CH3:28])[CH3:27]

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 149389872-(3-Aminophenyl)ethan-1-olHCID 223401634-Chloromethyl-2-(4-tert-butyl phenyl)thiazole

Produkt 1

HCID 223401293-{2-[2-(4-tert-Butyl-phenyl)-thiazol-4-ylmethoxy]-ethyl}-phenyl amineAusbeute 34,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3633615-Crown-5KatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 0.027 g (1 mmol) of 95% sodium hydride and 0.5 drop of 15-crown-5 in 20 mL of THF was added dropwise a solution of 0.139 g (1 mmol) of 3-(2-hydroxy ethyl)phenyl amine at 0° C. After stirring for 0.5 hr 0.28 g (1.1 mmol) of 4-chloromethyl-2-(4-tert-butyl phenyl)thiazole was added in one portion. The mixture was stirred at room temperature for 5 hr. At the end of this time, the solution was concentrated and the residue washed with 10 ml of saturated ammonium chloride and extracted 2 times with 30 mL of ethyl acetate. The organic layers were combined, dried (MgSO4) and concentrated to recover an oil, which was purified by column chromatography on SiO2 with 30% ethyl acetate:hexane elution to provide 0.125 g of product as an oil, used in the next step without further purification. NMR (400 MHz, DMSO-d6) δ 7.83 (d, J=8 Hz, 2H, ArH), 7.50 (d, J=8 Hz, 2H, ArH), 7.45 (s, 1H, N═CH) 7.08 (t, J=8 Hz, 1H, H5), 6.63 (d, J=8 Hz, 1H, H4), 6.54 (s, 1H, H2), 6.51 (d, J=8 Hz, 1H, H6) 4.59 (s, 2H, OCH2), 3.71 (t, J=7 Hz, 2H, OCH2), 2.87 (t, J=7 Hz, 2H, ArCH2), 1.30 (s, 9H, t-bu).

Aufarbeitung

  1. additionwas added in one portion
  2. concentrationAt the end of this time, the solution was concentrated
  3. washthe residue washed with 10 ml of saturated ammonium chloride
  4. extractionextracted 2 times with 30 mL of ethyl acetate
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customto recover an oil, which
  8. customwas purified by column chromatography on SiO2 with 30% ethyl acetate
  9. washhexane elution

Quellen und Nachweise

ORD-Eintrag
ord-4ddccf872829470bbdbd5e4166f27fea
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06930131B2

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