Water → 3-Fluoro-1,3-dihydro-1-methyl-7-chloro-5-phenyl-2H-1,4-benzodiazepin-2-one

HRID 1112092

Reaktionsgleichung

Reaktionsgleichung von HRID 1112092
O[CH:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]2[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:5]=2[N:4]([CH3:20])[C:3]1=[O:21].C(N(S(F)(F)[F:28])CC)C.O>C(Cl)Cl>[F:28][CH:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]2[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:5]=2[N:4]([CH3:20])[C:3]1=[O:21]

Komponenten

5

Edukt 3

HCID 962WaterHCID 5391TemazepamHCID 123472(Diethylamino)sulfur trifluoride

Produkt 1

HCID 126021203-Fluoro-1,3-dihydro-1-methyl-7-chloro-5-phenyl-2H-1,4-benzodiazepin-2-oneAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 12.1 g (0.04 mol) of 3-hydroxy-1,3-dihydro-1-methyl-7-chloro-5-phenyl-2H-1,4-benzodiazepin-2-one in 25 ml of anhydrous methylene chloride was added dropwise over a period of 15 min. to a stirred solution of 12.6 ml (0.1 mol) of diethylaminosulfur trifluoride in 300 ml of anhydrous methylene chloride cooled to -70°. The reaction mixture was allowed to warm slowly over a period of 45 min. to 5° and then poured into 500 ml of ice and water. The lower organic layer was separated, washed with water, dried over anhydrous magnesium sulfate, and evaporated to dryness under reduced pressure to give 10.9 g (90% yield) of crude product as a light yellow solid residue. Recrystallization from heptane gave 8.48 g (70% yield) of 3-fluoro-1,3-dihydro-1-methyl-7-chloro-5-phenyl-2H-1,4-benzodiazepin-2-one as colorless crystals: mp 138°-140°; 19F nmr (CCl3D) δ -161.7 ppm (d, J = 57 Hz); 1H nmr (CCl3D) δ 3.43 ppm (s, 3H), 5.54 ppm (d, J = 57 Hz, 1H), 7.5 ppm (m, 8H).

Aufarbeitung

  1. temperaturecooled to -70°
  2. temperatureto warm slowly over a period of 45 min. to 5°
  3. customThe lower organic layer was separated
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated to dryness under reduced pressure
  7. customto give 10.9 g (90% yield) of crude product as a light yellow solid residue
  8. customRecrystallization from heptane

Quellen und Nachweise

ORD-Eintrag
ord-4875f463a9804a8f84f0d2f88115b8d6
Quelldatensatz
uspto-grants-1978_10
Patentnummer
US04120856

Verknüpfte Notizen

Wird geladen…