Water → HCID 21866225, Verbindung

HRID 857786Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 857786
[N:1]([CH2:4][C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[C:12]1[C:16]([Cl:17])=[N:15][S:14][N:13]=1)=[N+]=[N-].O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH-].[K+]>C1COCC1.CO>[Cl:11][C:9]1[CH:8]=[CH:7][C:6]([C:12]2[C:16]([Cl:17])=[N:15][S:14][N:13]=2)=[C:5]([CH2:4][NH2:1])[CH:10]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 14797Potassium HydroxideHCID 21866197HCID 21866197, Verbindung

Produkt 1

HCID 21866225HCID 21866225, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-[2-(azidomethyl)-4-chlorophenyl]-4-chloro-1,2,5-thiadiazole (0.205 g, 0.72 mmol) and water (0.01 mL, 0.72 mmol) in THF (1.5 mL) was added triphenyl phosphine (0.188 g, 0.72 mmol). The solution was refluxed 1 h then stirred at ambient temperature for 16 h. The solution was reduced in vacuo and the residue was dissolved in MeOH. KOH (1 pellet) was added and the solution was refluxed 5 min. The solution was reduced in vacuo and partitioned between 1 M HCl and EtOAc. The aqueous phase was separated, basified with 1 M NaOH and extracted into ether. The organic phase was separated, dried (Na2SO4) and reduced in vacuo. The residue was purified by flash chromatography on silica (eluting with EtOAc/hexanes gradient, 5–10% EtOAc followed by 0.9% MeOH/0.1% NH4OH/chloroform). 1-[5-Chloro-2-(4-chloro-1,2,5-thiadiazole-3-yl)phenyl]methanamine was isolated as a yellow oil. MS m/z=260.5.

Aufarbeitung

  1. temperatureThe solution was refluxed 1 h
  2. temperaturethe solution was refluxed 5 min
  3. custompartitioned between 1 M HCl and EtOAc
  4. customThe aqueous phase was separated
  5. extractionextracted into ether
  6. customThe organic phase was separated
  7. dry with materialdried (Na2SO4)
  8. customThe residue was purified by flash chromatography on silica (eluting with EtOAc/hexanes gradient, 5–10% EtOAc followed by 0.9% MeOH/0.1% NH4OH/chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-563f947af26b42969b779b7000f47b33
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07144899B2

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