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9-(4-Chloro-2-fluoro-5-nitrophenyl)imino-8-thia-1,6-diazabicyclo[4.3.0]nonane-7-thione → 9-(5-Amino-4-chloro-2-fluorophenyl)imino-8-thia-1,6-diazabicyclo[4.3.0]nonane-7-thione

HRID 1164711
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1164711
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([N:11]=[C:12]2[N:20]3[N:15]([CH2:16][CH2:17][CH2:18][CH2:19]3)[C:14](=[S:21])[S:13]2)=[C:4]([F:22])[CH:3]=1>C(O)(=O)C.[Fe]>[NH2:8][C:7]1[C:2]([Cl:1])=[CH:3][C:4]([F:22])=[C:5]([N:11]=[C:12]2[N:20]3[N:15]([CH2:16][CH2:17][CH2:18][CH2:19]3)[C:14](=[S:21])[S:13]2)[CH:6]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 1

HCID 146229569-(4-Chloro-2-fluoro-5-nitrophenyl)imino-8-thia-1,6-diazabicyclo[4.3.0]nonane-7-thione

Produkt 1

HCID 146229579-(5-Amino-4-chloro-2-fluorophenyl)imino-8-thia-1,6-diazabicyclo[4.3.0]nonane-7-thioneAusbeute 79,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

To a stirred, hot (75° C.) mixture of 1.4 g (0.025 mole) of iron powder in 200 mL of acetic acid was added 1.5 g (0.0042 mole) of 9-(4-chloro-2-fluoro-5-nitrophenyl)imino-8-thia-1,6-diazabicyclo[4.3.0]nonane-7-thione. The mixture was stirred at 75° C. for one hour, then filtered and the filtrate evaporated under reduced pressure leaving a residue. The residue was partitioned between ethyl acetate and an aqueous, saturated sodium bicarbonate solution. The organic phase was separated, dried over anhydrous magnesium sulfate, and filtered. The filtrate was evaporated under reduced pressure to yield 1.1 g of 9-(5-amino-4-chloro-2-fluorophenyl)imino-8-thia-1,6-diazabicyclo[4.3.0]nonane-7-thione as a solid, mp 59°-61° C.

Aufarbeitung

  1. filtrationfiltered
  2. customthe filtrate evaporated under reduced pressure
  3. customleaving a residue
  4. customThe residue was partitioned between ethyl acetate
  5. customThe organic phase was separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customThe filtrate was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-83248548c50c4a038d5df084548c42cd
Quelldatensatz
uspto-grants-1990_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04906281

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