Benzoyl chloride → HCID 66973544, Verbindung

HRID 1469119Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1469119
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][N:5]([S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])[C:4](=[O:18])[N:3]=1.CCN(CC)CC.[C:26](Cl)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(Cl)Cl>[C:12]1([S:9]([N:5]2[CH:6]=[C:7]([F:8])[C:2]([NH:1][C:26](=[O:33])[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:3][C:4]2=[O:18])(=[O:10])=[O:11])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

5

Edukt 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 58138399HCID 58138399, Verbindung

Produkt 1

HCID 66973544HCID 66973544, VerbindungAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To an 8 mL screw-cap vial was added 4-amino-1-benzenesulfonyl-5-fluoro-1H-pyrimidin-2-one (200 mg, 0.74 mmol), CH2Cl2 (5 mL), Et3N (200 mg, 1.98 mmol), and benzoyl chloride (114 mg, 0.82 mmol). The mixture was shaken at room temperature for 2.5 h, evaporated under a stream of nitrogen, and partitioned between EtOAc and H2O. The organic phase was dried over MgSO4, filtered, and evaporated. The crude material was partially purified by normal phase chromatography (gradient, 10 to 50% EtOAc/petroleum ether), and fractions containing the major product were evaporated and recrystallized from EtOAc and petroleum ether to yield the title product as a white solid (112 mg, 41%): mp 150-151° C.; 1H NMR (300 MHz, CDCl3) δ 8.31-8.25 (m, 2H), 8.24 (d, J=5.8 Hz, 1H), 8.16-8.11 (m, 2H), 7.82-7.75 (m, 1H), 7.68-7.56 (m, 3H), 7.52-7.44 (m, 2H); ESIMS m/z 374 ([M+H]+), 372 ([M−H]−).

Aufarbeitung

  1. customTo an 8 mL screw-cap vial
  2. customevaporated under a stream of nitrogen
  3. custompartitioned between EtOAc and H2O
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude material was partially purified by normal phase chromatography (gradient, 10 to 50% EtOAc/petroleum ether), and fractions
  8. additioncontaining the major product
  9. customwere evaporated
  10. customrecrystallized from EtOAc and petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-3072d0a1f4fd4eb49bcbf8958202ac84
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006259B2

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