Hydrochloric Acid → HCID 135677442, Verbindung

HRID 263153

Reaktionsgleichung

Reaktionsgleichung von HRID 263153
Cl.[NH2:2][C:3]1[CH:4]=[C:5]([S:9]([F:12])(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1.Cl.[N:14]([O-])=O.[Na+].[Cl:18][C:19]1[C:20]([OH:27])=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH:22]=[O:23]>O.N1C=CC=CC=1>[Cl:18][C:19]1[C:20]([OH:27])=[C:21]([CH:24]=[C:25]([N:14]=[N:2][C:3]2[CH:8]=[CH:7][CH:6]=[C:5]([S:9]([F:12])(=[O:11])=[O:10])[CH:4]=2)[CH:26]=1)[CH:22]=[O:23]

Komponenten

7

Edukt 4

HCID 313Hydrochloric Acid2×HCID 77496Benzenesulfonyl fluoride, 3-amino-, hydrochloride (1:1)HCID 5196513-Chloro-2-hydroxybenzaldehydeHCID 23668193Sodium Nitrite

Produkt 1

HCID 135677442HCID 135677442, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

m-Aminobenzenesulfonyl fluoride hydrochloride (21.1 g, 0.099 mol) was slurried in hot 10% HCl (300 ml) and then cooled to 0° C. Sodium nitrite (7.0 g, 0.1 mol) was dissolved in 30 ml water and added dropwise to the acidic solution. Vigorous stirring was required to prevent the slurry from coagulating. The diazonium slurry was then added slowly to 500 ml of pyridine containing 3-chloro-2-hydroxy-benzaldehyde (16.0 g, 0.10 mol) at 0° C. The mixture was stirred 30 minutes and then slowly added to 1500 ml ice and hydrochloric acid. The resulting precipitate coagulated into one lump. The liquid was decanted off and the remaining tarry solid crushed and slurried in 50% HCl. The resulting solid was filtered off, washed with water and air dried, (21.1 g). Upon standing 72 hours, the decanted solution yielded an additional 2.8 g. Yield: 23.8 g (70%).

Aufarbeitung

  1. additionadded dropwise to the acidic solution
  2. stirringThe mixture was stirred 30 minutes
  3. customThe liquid was decanted off
  4. customthe remaining tarry solid crushed and slurried in 50% HCl
  5. filtrationThe resulting solid was filtered off
  6. washwashed with water and air
  7. customdried
  8. customthe decanted solution yielded an additional 2.8 g

Quellen und Nachweise

ORD-Eintrag
ord-1ec54e38ca794699aaba96952205f042
Quelldatensatz
uspto-grants-1979_05
Patentnummer
US04156609

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