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Sodium Carbonate → 2-(4,5-Dimethoxy-2-methoxymethoxyphenyl)-4-(2-pyridylmethyl)aminomethylbenzoxazole

HRID 855909
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 855909
Br[CH2:2][C:3]1[C:8]2[N:9]=[C:10]([C:12]3[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[CH:14][C:13]=3[O:22][CH2:23][O:24][CH3:25])[O:11][C:7]=2[CH:6]=[CH:5][CH:4]=1.[NH2:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1.C([O-])([O-])=O.[Na+].[Na+]>CC#N>[CH3:21][O:20][C:15]1[C:16]([O:18][CH3:19])=[CH:17][C:12]([C:10]2[O:11][C:7]3[CH:6]=[CH:5][CH:4]=[C:3]([CH2:2][NH:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=4)[C:8]=3[N:9]=2)=[C:13]([O:22][CH2:23][O:24][CH3:25])[CH:14]=1
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Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 195092-PyridinemethanamineHCID 219593354-Bromomethyl-2-(4,5-dimethoxy-2-methoxymethoxyphenyl)benzoxazole

Produkt 1

HCID 219593292-(4,5-Dimethoxy-2-methoxymethoxyphenyl)-4-(2-pyridylmethyl)aminomethylbenzoxazoleAusbeute 17,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342
Acetonitrile
Lösungsmittel

Versuchsvorschrift

A mixture of 6 (612 mg, 1.5 mmol), 2-(aminomethyl)pyridine (1.08 g, 10 mmol), and Na2CO3 (excess) in CH3CN (30 mL) was stirred overnight at room temperature. Insoluble material was removed by filtration and the filtrate was concentrated in vacuo. Water (20 mL) was added to the residue, which was extracted with ethyl acetate (20 mL) three times. The combined organic layer was washed with brine and water, dried over MgSO4, and evaporated. The resulting oily material was purified by silica gel column chromatography (CHCl3-ethyl acetate) to afford 7 as pale yellow oil (112 mg, 17%): 1H-NMR (500 MHz, CDCl3) δ3.56 (s, 3H), 3.95 (s, 3H), 3.97 (s, 3H), 4.02 (s, 2H), 4.30 (s, 2H), 5.27 (s, 2H), 6.85 (s, 1H), 7.15 (dd, 1H, J=7.5, 5.0 Hz), 7.28 (t, 1H, J=7.5 Hz), 7.33 (d, 1H, J=7.5 Hz), 7.42 (d, 1H, J=7.5 Hz), 7.47 (d, 1H, J=7.5 Hz), 7.64 (m, 2H), 8.55 (d, 1H, J=5.0 Hz).

Aufarbeitung

  1. customInsoluble material was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. additionWater (20 mL) was added to the residue, which
  4. extractionwas extracted with ethyl acetate (20 mL) three times
  5. washThe combined organic layer was washed with brine and water
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customThe resulting oily material was purified by silica gel column chromatography (CHCl3-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-3a7d1efe1e644536b4d5beb576ba9872
Quelldatensatz
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07262301B1

Notizen zur Reaktion

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