1-Chloro-4-phenylphthalazine → HCID 1386209, Verbindung

HRID 1471331Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1471331
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:4][N:3]=1.[NH2:18][C:19]1[CH:33]=[CH:32][C:22]2[N:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:24]=[N:25][C:21]=2[CH:20]=1>CC(O)C>[C:26]1([N:23]2[C:22]3[CH:32]=[CH:33][C:19]([NH:18][C:2]4[C:11]5[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=5)[C:5]([C:12]5[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=5)=[N:4][N:3]=4)=[CH:20][C:21]=3[N:25]=[CH:24]2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Komponenten

4

Edukt 2

HCID 2721091-Chloro-4-phenylphthalazineHCID 9653125-Amino-1-phenylbenzimidazole

Produkt 1

HCID 1386209HCID 1386209, VerbindungAusbeute 99,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A solution of 1-chloro-4-phenylphthalazine (156 mg, 0.65 mmol) and 5-amino-1-phenylbenzimidazole (4) (105 mg, 0.5 mmol) in i-PrOH (10 mL) is stirred at 95° C. under argon for 2 h. The reaction mixture is concentrated, diluted with sat. NaHCO3 (15 mL), and extracted with CHCl3 (100 mL). The extract is washed (brine) and dried. After solvent removal at reduced pressure, the residue is purified on silica gel (1% to 9% methanol/ethyl acetate) to give 206 mg (99%) of 5 as an orange solid, mp 265° C. IR 3285, 2842, 1615, 1476 cm−1; 1H NMR (CDCl3) δ 7.45-7.61 (m, 5H, 1-PhH), 7.62-7.77 (m, 6H, 4′-C6H5, 7-BenzimidH), 7.82 (dd, J=8.7, 2.1 Hz, 1H, 6-BenzimidH), 7.86-7.90 (m, 1H, 5′-PhthH), 7.91-7.98 (m, 1H, 6′-PhthH), 8.00-8.08 (m, 1H, 7′-PhthH), 8.50 (d, J=2.1 Hz, 1H, 4-BenzimidH), 8.56 (s, 1H, 2-BenzimidH), 8.72 (d, J=8.7 Hz, 1H, 8′-PhthH), 9.37 ppm (s, 1H, NH).

Aufarbeitung

  1. concentrationThe reaction mixture is concentrated
  2. additiondiluted with sat. NaHCO3 (15 mL)
  3. extractionextracted with CHCl3 (100 mL)
  4. washThe extract is washed (brine)
  5. customdried
  6. customAfter solvent removal at reduced pressure
  7. customthe residue is purified on silica gel (1% to 9% methanol/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-4c937f03d04c4d04957890f17d701a28
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09012217B2

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