1-Chloro-2,4-Dinitrobenzene → HCID 178484976, Verbindung

HRID 597239Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 597239
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1Cl)([O-:3])=[O:2].[C:14]([NH:16][C:17]([NH:22][CH3:23])=[N:18][CH2:19][CH2:20][SH:21])#[N:15]>C(O)C>[C:14]([NH:16][C:17]([NH:22][CH3:23])=[N:18][CH2:19][CH2:20][S:21][C:5]1[CH:6]=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])#[N:15]

Komponenten

4

Edukt 2

HCID 61-Chloro-2,4-DinitrobenzeneHCID 178485018HCID 178485018, Verbindung

Produkt 1

HCID 178484976HCID 178484976, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

A solution of cysteamine hydrochloride (5.68 g) in water (20 ml) was added to a suspension of N-cyano-N,S-dimethyl-isothiourea (6.46 g) in ethanol (100 ml). A solution of sodium hydroxide (4.0 g) in water (20 ml) was added to the mixture and the suspension was heated under reflux for 1 hour. The resulting clear solution was concentrated to remove ethanol, a little more water was added and the alkaline aqueous solution was extracted with ethyl acetate. The aqueous solution was adjusted to pH4 with hydrochloric acid and extracted with ethyl acetate. This latter organic extract was dried and evaporated to give N-cyano-N'-methyl-N"-(2-mercaptoethyl)guanidine (6.12 g) as a colourless oil. In order to characterise this product a solution of 2,4-dinitrochlorobenzene (7.7 g) in 95% ethanol (50 ml) was added to a solution of N-cyano-N'-methyl-N"-(2-mercaptoethyl)-guanidine (6.0 g) in 95% ethanol. The mixture was refluxed for 1 hour and cooled. The resulting crystalline solid (7.73 g) was collected and was triturated with a large volume of ether and was recrystallised from acetonitrile to afford N-cyano-N'-methyl-N"-[S-(2,4-dinitrophenyl)-2-mercaptoethyl]-guanidine, m.p. 210°-211° C.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 1 hour
  2. temperaturecooled
  3. customThe resulting crystalline solid (7.73 g) was collected
  4. customwas triturated with a large volume of ether
  5. customwas recrystallised from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-fb81a81b85cc4299b112171ebf4539b7
Quelldatensatz
uspto-grants-1977_03
Patentnummer
US04013678

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