Acetic Acid → 2-Nitro-1-phenylethyl pyrrolidine-1-carbodithioate

HRID 259452

Reaktionsgleichung

[N+:1]([CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([O-:3])=[O:2].[N:12]1([C:17]([S-:19])=[S:18])[CH2:16][CH2:15][CH2:14][CH2:13]1.[NH4+].C(O)(=O)C>CO>[N:12]1([C:17]([S:19][CH:5]([CH2:4][N+:1]([O-:3])=[O:2])[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[S:18])[CH2:16][CH2:15][CH2:14][CH2:13]1

Komponenten

Reaktionsbedingungen

Temperatur: 10 °C

Versuchsvorschrift

β-Nitrostyrene (7.5 grams, 0.050 mole) was added to a cooled (10° C.) stirred slurry of ammonium 1-pyrrolidinecarbodithioate (8.2 grams, 0.050 mole) in methanol (50 ml.). The temperature of the mixture fell to 5° C., then rapidly climbed to 10° C. The cooling bath was removed and the reaction temperature rose slowly to 22° C. Acetic acid (3.0 grams, 0.05 mole) was added, the slurry was cooled to 10° C. and the solid was filtered off, washed with water, and dried in air. The crude product melted at 108° - 116° C. and weighed 11.4 grams (77% yield). Repeated recrystallizations from cool acetone-methanol, hot acetone-2-propanol, and cool methylene chloride-toluene-hexane solutions gave pure α-(nitromethyl)benzyl 1-pyrrolidinecarbodithioate melting at 116° - 120° C. (sintering at 113° C.).

Aufarbeitung

customfell to 5° C.
customrapidly climbed to 10° C
customThe cooling bath was removed
customrose slowly to 22° C
temperaturethe slurry was cooled to 10° C.
filtrationthe solid was filtered off
washwashed with water
customdried in air
customrecrystallizations
temperaturefrom cool acetone-methanol, hot acetone-2-propanol
temperaturecool methylene chloride-toluene-hexane solutions

Quellen und Nachweise

ORD-Eintrag: ord-7efb0e60deca4a4081e2eea946282b06
Quelldatensatz: uspto-grants-1977_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04038288

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