Sulfuric Acid → 8-Amino-1-naphthalenethiol

HRID 235680Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 235680
[CH:1]1[CH:6]=[C:5]2[NH:7][S:8]([C:11]3=[CH:12][CH:13]=[CH:14][C:3](=[C:4]23)[CH:2]=1)(=O)=O.[H-].COCCO[Al+]OCCOC.[Na+].[H-].C1(C)C=CC=CC=1.S(=O)(=O)(O)O>C(COC)OC.O>[NH2:7][C:5]1[CH:6]=[CH:1][CH:2]=[C:3]2[C:4]=1[C:11]([SH:8])=[CH:12][CH:13]=[CH:14]2

Komponenten

7

Edukt 4

HCID 1118Sulfuric AcidHCID 1140TolueneHCID 690522H-Naphth(1,8-cd)isothiazole 1,1-dioxideHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

Produkt 1

HCID 125743828-Amino-1-naphthalenethiolAusbeute 87,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

To a solution of 2.0 g of 1,8-naphthosultam in 7 mL of dimethoxyethane was added dropwise under gentle reflux a solution of 11.5 mL of sodium bis(2-methoxyethoxy)aluminum hydride in toluene (3.4 mol solution in toluene) over a period of 15 minutes, then stirred at reflux for 17 hours. The mixture was cooled in an ice-bath, 5 mL of water were added dropwise then the solution was neutralized with 4N sulfuric acid (pH~7) and extracted with ether (3×75 mL). The combined ether solutions were washed with water (75 mL) then dried (magnesium sulfate) and removal of the solvent gave 1.5 g of 8 -amino-1-napthalenethiol. The thiol was recrystallized from ether--petroleum ether to afford 1.3 g of 8-amino-1-naphthalenethiol, mp. 69°-72°.

Aufarbeitung

  1. temperatureat reflux for 17 hours
  2. temperatureThe mixture was cooled in an ice-bath
  3. extractionextracted with ether (3×75 mL)
  4. washThe combined ether solutions were washed with water (75 mL)
  5. customthen dried
  6. custom(magnesium sulfate) and removal of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-b79cbf5aff1142e1b1d1e112538923ef
Quelldatensatz
uspto-grants-1987_02
Patentnummer
US04640930

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