Acetonitrile → 4-Ethylthio-1-(3-methoxycarbonyl-2-thioureido)-2-nitrobenzene

HRID 258762Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 258762
[S-:1][C:2]#[N:3].[K+].C(#N)C.Cl[C:9]([O:11][CH3:12])=[O:10].[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([S:20][CH2:21][CH3:22])=[CH:16][C:15]=1[N+:23]([O-:25])=[O:24]>O>[CH2:21]([S:20][C:17]1[CH:18]=[CH:19][C:14]([NH:13][C:2]([NH:3][C:9]([O:11][CH3:12])=[O:10])=[S:1])=[C:15]([N+:23]([O-:25])=[O:24])[CH:16]=1)[CH3:22]

Komponenten

6

Edukt 4

HCID 6342AcetonitrileHCID 6586Methyl chloroformateHCID 516872Potassium thiocyanateHCID 203720451-Amino-4-ethylthio-2-nitrobenzene

Produkt 1

HCID 203720534-Ethylthio-1-(3-methoxycarbonyl-2-thioureido)-2-nitrobenzeneAusbeute 39,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

A mixture of dry potassium thiocyanate (25.65 g.) and acetonitrile (320 ml.) was cooled to 10° C. and treated during 5 minutes with methyl chloroformate (25.0 g.). The mixture was stirred at room temperature for 2 hours. 1-Amino-4-ethylthio-2-nitrobenzene (22.45 g.) was then added to the mixture at 10°-15° C. The suspension was stirred for 3 hours at room temperature and allowed to stand overnight. It was then poured into water (1.6 liters) and the solid which precipitated was filtered off, washed with water and recrystallised from a mixture of methanol and ethanol, to give 4-ethylthio-1-(3-methoxycarbonyl-2-thioureido)-2-nitrobenzene (14.0 g.), m.p. 152° C.

Aufarbeitung

  1. stirringThe suspension was stirred for 3 hours at room temperature
  2. waitto stand overnight
  3. customthe solid which precipitated
  4. filtrationwas filtered off
  5. washwashed with water
  6. customrecrystallised from a mixture of methanol and ethanol

Quellen und Nachweise

ORD-Eintrag
ord-c37ed3ac3f494bd9bfe7ce054493466d
Quelldatensatz
uspto-grants-1977_07
Patentnummer
US04034107

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