Ammonium Chloride → 3-Amino-4-[(3-chloropyrazin-2-yl)thio]benzyl alcohol

HRID 1059293Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1059293
[Cl:1][C:2]1[C:3]([S:8][C:9]2[CH:16]=[CH:15][C:12]([CH2:13][OH:14])=[CH:11][C:10]=2[N+:17]([O-])=O)=[N:4][CH:5]=[CH:6][N:7]=1.[Cl-].[NH4+]>O1CCCC1.CC(O)C.O.[Fe]>[NH2:17][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:9]=1[S:8][C:3]1[C:2]([Cl:1])=[N:7][CH:6]=[CH:5][N:4]=1)[CH2:13][OH:14]

Komponenten

7

Edukt 2

HCID 25517Ammonium ChlorideHCID 114379644-[(3-Chloropyrazin-2-yl)thio]-3-nitrobenzyl alcohol

Produkt 1

HCID 235641353-Amino-4-[(3-chloropyrazin-2-yl)thio]benzyl alcoholAusbeute 102,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23925IronKatalysatorHCID 962WaterLösungsmittelHCID 3776IsopropanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1.60 g of 4-[(3-chloropyrazin-2-yl)thio]-3-nitrobenzyl alcohol was dissolved in a solvent mixture of tetrahydrofuran (20 ml)/2-propanol (20 ml)/water (7 ml). After adding 0.16 g of ammonium chloride and 1.50 g of iron powder, the resulting mixture was heated under reflux for 30 minutes. Then the reaction mixture was filtered through celite and concentrated under reduced pressure. After adding ethanol, the reaction mixture was concentrated under reduced pressure. Then tetrahydrofuran was added to the residue and the insoluble matters were separated by filtration. After distilling off the solvent under reduced pressure, 1.47 g of the title compound was obtained as yellow crystals.

Aufarbeitung

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 30 minutes
  3. filtrationThen the reaction mixture was filtered through celite and
  4. concentrationconcentrated under reduced pressure
  5. additionAfter adding ethanol
  6. concentrationthe reaction mixture was concentrated under reduced pressure
  7. additionThen tetrahydrofuran was added to the residue
  8. customthe insoluble matters were separated by filtration
  9. distillationAfter distilling off the solvent under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9374dddd8b6943478e4aa9e8b249cda0
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06518423B1

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