beta,beta'-Thiodipropionitrile → Acetamide, N-(2-(2-(2-cyano-4,6-dinitrophenyl)diazenyl)-5-(diethylamino)phenyl)-

HRID 1704198

Reaktionsgleichung

Reaktionsgleichung von HRID 1704198
[C:1](CCSCCC#N)#[N:2].[C:10]([NH:13][C:14]1[CH:15]=[C:16]([CH:22]=[CH:23][C:24]=1[N:25]=[N:26][C:27]1[C:32]([N+:33]([O-:35])=[O:34])=[CH:31][C:30]([N+:36]([O-:38])=[O:37])=[CH:29][C:28]=1Br)[N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])(=[O:12])[CH3:11].[C-]#N.[Na+]>O>[C:10]([NH:13][C:14]1[CH:15]=[C:16]([CH:22]=[CH:23][C:24]=1[N:25]=[N:26][C:27]1[C:32]([N+:33]([O-:35])=[O:34])=[CH:31][C:30]([N+:36]([O-:38])=[O:37])=[CH:29][C:28]=1[C:1]#[N:2])[N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])(=[O:12])[CH3:11]

Komponenten

5

Edukt 3

HCID 8151beta,beta'-ThiodipropionitrileHCID 8929Sodium CyanideHCID 104287Acetamide, N-[2-[2-(2-bromo-4,6-dinitrophenyl)diazenyl]-5-(diethylamino)phenyl]-

Produkt 1

HCID 90383Acetamide, N-(2-(2-(2-cyano-4,6-dinitrophenyl)diazenyl)-5-(diethylamino)phenyl)-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Into a reactor there are introduced 765 parts of bis-(β-cyanoethyl) sulfide, followed by 14.35 parts of cuprous bromide. On heating to 60° C. with continuous stirring, a brownish-yellow solution of the copper complex is obtained. 95.8 parts of 3-acetamido-4-(2'bromo-4',6'-dinitrophenylazo)N,N-diethylaniline are added, and the temperature is raised to 115° C. Raising the temperature to 115° C. causes the compound to completely dissolve. At ths temperature, a solution of 10.8 parts of sodium cyanide in 40 parts of water is introduced into the reactor during a period of 20 minutes, allowing the steam to escape. Stirring is continued for a further 20 to 30 minutes while verifying by thin layer chromatography that the starting organic bromo-derivative is absent. The reaction mass is cooled to 30-35° C., which causes crystallization of the dyestuff. The resultant product is filtered off, washed with water to displace the solvent contained in the paste, and dried. 80.2 parts of 3-acetamido-4 -(2'-cyano-4',6'-dinitro-phenylazo)-N,N-diethylaniline are obtained. The titre (purity) of this product is 98.5% and it contains a copper concentration of less than 3000 parts per million. The wash water is introduced into a decanter, and the organic solvent part is withdrawn and reunited with the fraction of solvent obtained during filtration. There are thus recovered 720 parts of bis-(β-cyanoethyl) sulfide which contain 4.35 parts of the cyanoazo dyestuff (giving an overall balance of the reaction of 98%) and 5.75 parts of copper (which corresponds to a recovery of 91% of the initial copper complex.

Aufarbeitung

  1. customa brownish-yellow solution of the copper complex is obtained
  2. temperaturethe temperature is raised to 115° C
  3. temperatureRaising the temperature to 115° C.
  4. dissolutionto completely dissolve
  5. temperatureThe reaction mass is cooled to 30-35° C.
  6. customcrystallization of the dyestuff
  7. filtrationThe resultant product is filtered off
  8. washwashed with water
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-496d695b90a34ee195963011f1629487
Quelldatensatz
uspto-grants-1978_11
Patentnummer
US04126610

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