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3-(n-Octyloxy)-4-(p-toluenesulfonyl)aminoaniline → 3-(n-Octyloxy)-4-(p-toluenesulfonyl)aminobenzenediazonium hexafluorophosphate

HRID 248795
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 248795
[CH2:1]([O:9][C:10]1[CH:11]=[C:12]([CH:14]=[CH:15][C:16]=1[NH:17][S:18]([C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1)(=[O:20])=[O:19])[NH2:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[N:28]([O-])=O.[Na+].[F:32][P-:33]([F:38])([F:37])([F:36])([F:35])[F:34].[K+]>CO.Cl.O>[F:32][P-:33]([F:38])([F:37])([F:36])([F:35])[F:34].[CH2:1]([O:9][C:10]1[CH:11]=[C:12]([N+:13]#[N:28])[CH:14]=[CH:15][C:16]=1[NH:17][S:18]([C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1)(=[O:19])=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 197621433-(n-Octyloxy)-4-(p-toluenesulfonyl)aminoanilineHCID 23668193Sodium NitriteHCID 23688904Potassium hexafluorophosphate

Produkt 1

HCID 197621383-(n-Octyloxy)-4-(p-toluenesulfonyl)aminobenzenediazonium hexafluorophosphateAusbeute 88,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313
Hydrochloric Acid
Lösungsmittel
HCID 887MethanolLösungsmittel
HCID 962WaterLösungsmittel2×

Versuchsvorschrift

Then, 39 g of 3-(n-octyloxy)-4-(p-toluenesulfonyl)aminoaniline was dissolved in a mixed solution of 300 ml of methanol and 25.3 ml of concentrated hydrochloric acid. The solution was cooled to -10° to -5° C., and a solution of 6.9 g of sodium nitrite in 14 ml of water was added thereto in several seconds and, after 10 minutes, 18.5 g of powdery potassium hexafluorophosphate was added thereto. Thereafter, 150 ml of water was dropwise added thereto over about 30 minutes, and the resulting mixture was stirred for about one hour while keeping the internal temperature at about 5° C. 3-(n-Octyloxy)-4-(p-toluene-sulfonyl)aminobenzenediazonium hexafluorophosphate precipitated as crystals was filtered out, and washed with a mixed solvent of methanol-water to obtain 48.4 g of 3-(n-octyloxy)-4-(p-toluenesulfonyl)aminobenzenediazonium hexafluorophosphate.

Aufarbeitung

  1. temperatureThe solution was cooled to -10° to -5° C.
  2. waitin several seconds
  3. waitover about 30 minutes
  4. customat about 5° C
  5. custom3-(n-Octyloxy)-4-(p-toluene-sulfonyl)aminobenzenediazonium hexafluorophosphate precipitated as crystals
  6. filtrationwas filtered out
  7. washwashed with a mixed solvent of methanol-water

Quellen und Nachweise

ORD-Eintrag
ord-d7f2e8a791ff4a58a4c479771fadd5dc
Quelldatensatz
uspto-grants-1993_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05212042

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