Stannous Chloride → 5-benzenesulfonyl-1H-indazol-3-ylamine

HRID 1640967Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1640967
[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:12])=[O:11])=[CH:6][C:3]=1[C:4]#[N:5].[N:19]([O-])=O.[Na+].Cl[Sn]Cl>Cl.O>[C:13]1([S:10]([C:7]2[CH:6]=[C:3]3[C:2](=[CH:9][CH:8]=2)[NH:1][N:5]=[C:4]3[NH2:19])(=[O:12])=[O:11])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Komponenten

6

Edukt 3

HCID 24479Stannous ChlorideHCID 214324362-Amino-5-benzenesulfonyl-benzonitrileHCID 23668193Sodium Nitrite

Produkt 1

HCID 667361655-benzenesulfonyl-1H-indazol-3-ylamineAusbeute 40,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittel2×HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
4 °C

Versuchsvorschrift

2-Amino-5-benzenesulfonyl-benzonitrile (0.81 g, 3.15 mmol) in 37% HCl (5 mL) was treated dropwise at 4° C. with NaNO2 (261 mg, 3.78 mmol) in 5 mL of water. After 1.75 hours the suspension was added dropwise to a solution of SnCl2 (4.88 g, 25.21 mmol) in 5 mL of 37% HCl. After stirring at 4° C. for 3 hours the solid was filtered, taken up with water (30 mL) and boiled for 1.5 hours. The hot mixture was filtered and washed thoroughly with boiling water. The filtrate was cooled to 4° C. and treated under stirring with 17% NaOH (approximately 5 mL) dropwise. After overnight cooling in a fridge the solid was filtered and washed with water to neutral pH affording 0.348 g of title compound (40% yield).

Aufarbeitung

  1. filtrationwas filtered
  2. waitboiled for 1.5 hours
  3. filtrationThe hot mixture was filtered
  4. washwashed thoroughly with boiling water
  5. temperatureThe filtrate was cooled to 4° C.
  6. additiontreated
  7. stirringunder stirring with 17% NaOH (approximately 5 mL) dropwise
  8. temperatureAfter overnight cooling in a fridge the solid
  9. filtrationwas filtered
  10. washwashed with water to neutral pH

Quellen und Nachweise

ORD-Eintrag
ord-059d09c348014e7cb318c08f3617d40c
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08114865B2

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