Hydrochloric Acid → 4-(((2,4-Dichlorophenyl)methyl)amino)benzenesulfonic acid

HRID 1065093

Reaktionsgleichung

Reaktionsgleichung von HRID 1065093
[S:1]([OH:11])(=[O:10])([C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1)=[O:2].O.O.O.C([O-])(=O)C.[Na+].[Cl:20][C:21]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:22]=1[CH2:23]Cl.Cl>O.C(#N)C>[Cl:20][C:21]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:22]=1[CH2:23][NH:9][C:6]1[CH:5]=[CH:4][C:3]([S:1]([OH:11])(=[O:10])=[O:2])=[CH:8][CH:7]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 72122,4-Dichlorobenzyl chlorideHCID 8479Sulfanilic acidHCID 23665404Sodium Acetate Trihydrate

Produkt 1

HCID 128529254-(((2,4-Dichlorophenyl)methyl)amino)benzenesulfonic acidAusbeute 55,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

To a mixture of 52.0 g (0.30 mole) of sulfanilic acid in 225 ml of warm water was added 83 g (0.61 mole) of sodium acetate trihydrate and 75 ml of acetonitrile. Then a solution of 37.1 g (0.19 mole) of 2,4-dichlorobenzyl chloride in 75 ml of acetonitrile was added and the resulting solution refluxed for 31/2 hrs, followed by the dropwise addition of 50 ml of conc. HCl while simultaneously removing 75 ml of acetonitrile by distillation. The reaction mixture was filtered while hot (80° C.) and the same purification sequence utilized as described in the previous example, which gave 34.91 g (55.3% yield) of purified 4-(((2,4-dichlorophenyl)methyl)amino)benzenesulfonic acid as a white powder having a melting point greater than 275° C.

Aufarbeitung

  1. temperaturethe resulting solution refluxed for 31/2 hrs
  2. customwhile simultaneously removing 75 ml of acetonitrile
  3. distillationby distillation
  4. filtrationThe reaction mixture was filtered while hot (80° C.)

Quellen und Nachweise

ORD-Eintrag
ord-b62fc82af7c442a1968e2f10af7e9534
Quelldatensatz
uspto-grants-1982_05
Patentnummer
US04328244

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