(Diethylamino)sulfur trifluoride → HCID 13125992, Verbindung

HRID 1389816Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1389816
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[CH:9](O)[N:8]=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])[C:6]=2[CH:21]=1.C(N(S(F)(F)[F:28])CC)C>C(Cl)Cl>[F:28][CH:9]1[N:8]=[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])[C:6]2[CH:21]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=2[NH:11][C:10]1=[O:12]

Komponenten

4

Edukt 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 131260123-Hydroxyflubromazepam

Produkt 1

HCID 13125992HCID 13125992, VerbindungAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A stirred suspension of 4.2 g (0.012 mole) of 7-bromo-5-(2-fluorophenyl)-1,3-dihydro-3-hydroxy-2H-1,4-benzodiazepin-2-one in 200 ml methylene chloride was cooled to -70°, and 5 ml (0.04 mole) of diethylaminosulfur trifluoride was added dropwise. The reaction mixture was allowed to warm to -10°, and held at this temperature until most of the solid had dissolved. The reaction mixture was poured into ice-water and stirred vigorously. The organic layer was separated, washed with water, dried (MgSO4) and evaporated to dryness under reduced pressure. The residue was recrystallized from benzene-hexane to give 3.12 g of 3-fluoro-7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one as light yellow crystals: mp 195°-197° (dec.); 19F nmr (DMSO-d6) δ -113.0 ppm (m, 1F) and -162.1 ppm (d, J=56 Hz, 1F), 1H nmr (DMSO-d6) δ 5.88 ppm (d, J=56 Hz, 1H), 7.2-7.9 ppm (m, 7H), 11.2 ppm (NH).

Aufarbeitung

  1. temperaturewas cooled to -70°
  2. temperatureto warm to -10°
  3. dissolutionhad dissolved
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried (MgSO4)
  7. customevaporated to dryness under reduced pressure
  8. customThe residue was recrystallized from benzene-hexane

Quellen und Nachweise

ORD-Eintrag
ord-ae362d2afafb4dac92b9d83ba06ac27d
Quelldatensatz
uspto-grants-1981_01
Patentnummer
US04246270

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