2,6-Dichloropyrazine → N-(4-(6-Chloropyrazin-2-yloxy)naphthalen-1-yl)acetamide

HRID 16278

Reaktionsgleichung

Reaktionsgleichung von HRID 16278
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH:12][C:13](=[O:15])[CH3:14])=[CH:4][CH:3]=1.[Cl:16][C:17]1[CH:22]=[N:21][CH:20]=[C:19](Cl)[N:18]=1>>[Cl:16][C:17]1[N:18]=[C:19]([O:1][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([NH:12][C:13](=[O:15])[CH3:14])=[CH:4][CH:3]=2)[CH:20]=[N:21][CH:22]=1

Komponenten

3

Edukt 2

HCID 785042,6-DichloropyrazineHCID 235848N-(4-hydroxynaphthalen-1-yl)acetamide

Produkt 1

HCID 59343458N-(4-(6-Chloropyrazin-2-yloxy)naphthalen-1-yl)acetamideAusbeute 68,2 %

Versuchsvorschrift

Method DD was followed (in a round-bottomed flask, reaction time: 20 hours) with N-(4-hydroxynaphthalen-1-yl)acetamide (1.22 g, 6.08 mmol) and 2,6-dichloropyrazine (1.09 g, 7.30 mmol). The DMF was evaporated in vacuo. The resulting crude was dissolved in a mixture (hot) of AcOEt (25 mL) and acetone (175 mL) and filtered. The volume of the filtrate was reduced to 100 mL and this filtrate crystallised upon storage at low temperature to yield the title compound (1.30 g). Yield: 68%. 1H NMR (500 MHz, DMSO-d6) δ 2.21 (s, 3H), 7.42 (d, 1H, J=8.2 Hz), 7.57 (t, 1H, J=7.5 Hz), 7.64 (t, 1H, J=7.6 Hz), 7.72 (d, 1H, J=8.1 Hz), 7.90 (d, 1H, J=8.3 Hz), 8.16 (d, 1H, J=8.5 Hz), 8.52 (s, 1H), 8.72 (s, 1H), 10.02 (s, 1H). 13C NMR (125.8 MHz, DMSO-d6) δ 23.42, 117.59, 121.40, 121.65, 123.42, 126.53, 126.71, 126.85, 128.90, 131.85, 133.59, 137.50, 144.40, 145.04, 158.92, 169.04. m/z 314.0 [(M+H)+ calcd for C16H12ClN3O2 313.1].

Aufarbeitung

  1. customThe DMF was evaporated in vacuo
  2. dissolutionThe resulting crude was dissolved in a mixture (hot) of AcOEt (25 mL) and acetone (175 mL)
  3. filtrationfiltered
  4. customthis filtrate crystallised upon storage at low temperature

Quellen und Nachweise

ORD-Eintrag
ord-63cbd827c7844c0faa9de21a8c973c2c
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737152B2

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