Sodium Hydroxide → methyl 2-(N-tert-butylsulfamoyl)-4-hydrazinobenzoate

HRID 581656

Reaktionsgleichung

Reaktionsgleichung von HRID 581656
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([S:12](=[O:19])(=[O:18])[NH:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:3]=1.[N:20]([O-])=O.[Na+].O.O.Cl[Sn]Cl.[OH-].[Na+].C([O-])(O)=O.[Na+]>Cl.O>[C:14]([NH:13][S:12]([C:4]1[CH:3]=[C:2]([NH:1][NH2:20])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])(=[O:19])=[O:18])([CH3:16])([CH3:15])[CH3:17]

Komponenten

8

Edukt 5

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 10946074methyl 4-amino-2-(N-tert-butylsulfamoyl)benzoateHCID 23668193Sodium Nitrite

Produkt 1

HCID 21716182methyl 2-(N-tert-butylsulfamoyl)-4-hydrazinobenzoateAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittel3×HCID 962WaterLösungsmittel

Versuchsvorschrift

25.0 g (0.087 mol) of methyl 4-amino-2-(N-tert-butylsulfamoyl)benzoate are suspended in a mixture of 150 ml of concentrated HCl and 130 ml of water. A solution of 7.8 g (0.114 mol) of sodium nitrite is added dropwise at 0-5° C. A small amount of undissolved constituents are filtered off cold and the still cold diazonium salt solution is allowed to run slowly at 0° C. into a suspension of 55.0 g (0.244 mol) of SnCl2.2H2O in 55 ml of concentrated HCl. The mixture is subsequently stirred for 30 minutes and is then left to stand for 15 hours, while cooling with ice. Most of the HCl is first neutralized by addition of 6 N NaOH and the pH is then brought to about 6 with solid NaHCO3. The mixture is extracted several times with ethyl acetate, the extracts are dried and the solvent is removed in vacuo. After trituration of the residue with diisopropyl ether and drying, 18.3 g (70% of theory) of methyl 2-(N-tert-butylsulfamoyl)-4-hydrazinobenzoate of melting point 133-136° C. are obtained.

Aufarbeitung

  1. filtrationA small amount of undissolved constituents are filtered off cold
  2. waitis then left
  3. waitto stand for 15 hours
  4. temperaturewhile cooling with ice
  5. extractionThe mixture is extracted several times with ethyl acetate
  6. customthe extracts are dried
  7. customthe solvent is removed in vacuo
  8. dry with materialAfter trituration of the residue with diisopropyl ether and drying

Quellen und Nachweise

ORD-Eintrag
ord-169d15d6fcd7419582442516665faff0
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05922645

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