O-Phenylenediamine → 2-Amino-1-(2-mercapto-2-methylpropylamino)benzene
Reaktionsgleichung
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[CH3:9][C:10]1([S:13][CH2:12]1)[CH3:11]>CCOCC>[NH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[NH:8][CH2:9][C:10]([SH:13])([CH3:12])[CH3:11]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
o-Phenylenediamine (15.31 g, 1.42×10-1 mol, 100 M%) and 12.46 g (1.42×10-1 mol, 100 M%) isobutylene sulfide (Synder et al, J. Am. Chem. Soc. 69: 2672-2674, 1947) were mixed in a Parr bomb and heated in an oven at 80° C. for 18 hr. The bomb was cooled to room temperature and then opened. The crude brown oil contained some solid. The mixture was dissolved in 150 ml ether (some white solid did not dissolve), washed with saturated aqueous NaCl solution, and the solvent was removed on the rotary evaporator. The oily residue was placed on flash silic in a 600 ml sintered glass funnel and eluted with 500 ml portion of hexane, 90% hexane/ether, twice with 80% hexane/ether and twice with 50% hexane/ether. Evaporation of the first 50:50 hexane/ether fraction gave 7.36 g (26.5%) of 2-amino-1-(2-mercapto-2-methylpropylamino)benzene as a waxy crystalline product, mp 38°-40° C.
Aufarbeitung
- temperatureThe bomb was cooled to room temperature
- dissolutiondid not dissolve),
- washwashed with saturated aqueous NaCl solution
- customthe solvent was removed on the rotary evaporator
- customThe oily residue was placed on flash silic in a 600 ml sintered glass funnel
- washeluted with 500 ml portion of hexane, 90% hexane/ether, twice with 80% hexane/ether and twice with 50% hexane/ether
- customEvaporation of the first 50:50 hexane/ether fraction
Quellen und Nachweise
- ORD-Eintrag
- ord-e4a45165eb42407bbf9151991ed89bd1
- Quelldatensatz
- uspto-grants-1992_01
- Patentnummer
- US05080884
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