Diphosgene → 6-fluoro-5-isocyanato-3-(5-methyl-1,2,4-oxadiazol-3-ylmethyl)-2(3H)-benzothiazolone

HRID 1199621Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1199621
[NH2:1][C:2]1[C:3]([F:19])=[CH:4][C:5]2[S:9][C:8](=[O:10])[N:7]([CH2:11][C:12]3[N:16]=[C:15]([CH3:17])[O:14][N:13]=3)[C:6]=2[CH:18]=1.Cl[C:21](OC(Cl)(Cl)Cl)=[O:22]>O1CCOCC1>[F:19][C:3]1[C:2]([N:1]=[C:21]=[O:22])=[CH:18][C:6]2[N:7]([CH2:11][C:12]3[N:16]=[C:15]([CH3:17])[O:14][N:13]=3)[C:8](=[O:10])[S:9][C:5]=2[CH:4]=1

Komponenten

4

Edukt 2

HCID 10426DiphosgeneHCID 199794815-amino-6-fluoro-3-(5-methyl-1,2,4-oxadiazol-3-ylmethyl)-2(3H)-benzothiazolone

Produkt 1

HCID 199795066-fluoro-5-isocyanato-3-(5-methyl-1,2,4-oxadiazol-3-ylmethyl)-2(3H)-benzothiazoloneAusbeute 100,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 5-amino-6-fluoro-3-(5-methyl-1,2,4-oxadiazol-3-ylmethyl)-2(3H)-benzothiazolone (1.33 g) and dioxane (23 g) was prepared. To this mixture was dropwise added trichloromethyl chloroformate (1 g). The reaction mixture was heated under refluxing for 3 hours. The components with lower boiling points were distilled off, and the residue was dissolved in toluene (50 ml). The resulting solution was concentrated under a reduced pressure to dryness, so that the aimed compound, i.e. 6-fluoro-5-isocyanato-3-(5-methyl-1,2,4-oxadiazol-3-ylmethyl)-2-(3H)-benzothiazolone (1.46 g) was obtained. m.p. 125°-127° C.

Aufarbeitung

  1. customwas prepared
  2. temperatureThe reaction mixture was heated
  3. temperatureunder refluxing for 3 hours
  4. distillationThe components with lower boiling points were distilled off
  5. dissolutionthe residue was dissolved in toluene (50 ml)
  6. concentrationThe resulting solution was concentrated under a reduced pressure to dryness, so that the aimed compound

Quellen und Nachweise

ORD-Eintrag
ord-68daeea53608432c880bdacaa5416215
Quelldatensatz
uspto-grants-1990_02
Patentnummer
US04902335

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