Hydrazine hydrate (1:1) → 3-(Tert-butyldiphenylsilyloxymethyl)-2,4-dichloroaniline

HRID 564938

Reaktionsgleichung

Reaktionsgleichung von HRID 564938
[Si:1]([O:18][CH2:19][C:20]1[C:25]([Cl:26])=[CH:24][CH:23]=[C:22]([N+:27]([O-])=O)[C:21]=1[Cl:30])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN>CO.O>[NH2:27][C:22]1[C:21]([Cl:30])=[C:20]([CH2:19][O:18][Si:1]([C:14]([CH3:16])([CH3:15])[CH3:17])([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:25]([Cl:26])=[CH:24][CH:23]=1

Komponenten

5

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 117981851-(Tert-butyldiphenylsilyloxymethyl)-2,6-dichloro-3-nitrobenzene

Produkt 1

HCID 105987193-(Tert-butyldiphenylsilyloxymethyl)-2,4-dichloroanilineAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a stirred mixture of 1-(tert-butyldiphenylsilyloxymethyl)-2,6-dichloro-3-nitrobenzene (433 mg), ferric chloride hexahydrate (17.5 mg) and activated carbon (17.5 mg) in a mixture of methanol (2.78 ml) and water (0.69 ml) was added hydrazine monohydrate (0.135 ml) dropwise at 60-70° C. After the addition was finished, the mixture was refluxed for half an hour. The mixture was allowed to cool and filtered. The filtrate was concentrated in vacuo. The residue was extracted with dichloromethane and the organic phase was dried over anhydrous magnesium sulfate. After being filtered, the filtrate was concentrated in vacuo and the resulting residue was washed with n-hexane to give 3-amino-1-(tert-butyldiphenylsilyloxymethyl)-2,6-dichlorobenzene (348 mg) as a white mass.

Aufarbeitung

  1. additionAfter the addition
  2. temperaturethe mixture was refluxed for half an hour
  3. temperatureto cool
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. extractionThe residue was extracted with dichloromethane
  7. dry with materialthe organic phase was dried over anhydrous magnesium sulfate
  8. filtrationAfter being filtered
  9. concentrationthe filtrate was concentrated in vacuo
  10. washthe resulting residue was washed with n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-fe43b34577fd4d0bb7678632f93f37ad
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06169095A

Verknüpfte Notizen

Wird geladen…