Methanol → HCID 178477621, Verbindung

HRID 262527

Reaktionsgleichung

Reaktionsgleichung von HRID 262527
S(S([O-])=O)([O-])=[O:2].[Na+].[Na+].[N+](NC1C=CC=CC=1)([O-])=O.[CH2:19]([S:21][CH2:22][C:23]1[CH:36]=[CH:35][C:26]2[NH:27][C:28]([NH:30][C:31](=[O:34])[O:32][CH3:33])=[N:29][C:25]=2[CH:24]=1)[CH3:20].CO>C(O)C.O.[OH-].[NH4+].C(O)(=O)C>[CH2:19]([S:21]([CH2:22][C:23]1[CH:36]=[CH:35][C:26]2[NH:27][C:28]([NH:30][C:31](=[O:34])[O:32][CH3:33])=[N:29][C:25]=2[CH:24]=1)=[O:2])[CH3:20]

Komponenten

9

Edukt 4

HCID 887MethanolHCID 24489Sodium Dithionite2×HCID 61191N-NitroanilineHCID 178477414HCID 178477414, Verbindung

Produkt 1

HCID 178477621HCID 178477621, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 176Acetic AcidKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 14923Ammonium HydroxideLösungsmittel

Versuchsvorschrift

To the residue dissolved in 100 ml 95% ethanol is added sodium dithionite (9.4 g, 54 mmol) dissolved in 60 ml water and 15 ml concentrated ammonium hydroxide. After refluxing for 5 minutes, portions of sodium dithionite (1 g in 10 ml water and 2 ml ammonium hydroxide) are added until the orange nitroaniline color disappears. The reaction mixture is reduced to one-half volume by evaporation, basified with 20 ml 10% sodium hydroxide, and extracted with chloroform (X 5). The chloroform washings are dried (Na2SO4) and evaporated. The residue, 3.3 g (16.1 mmol) of the thiopseudourea from Example 1, part D, 6 drops of acetic acid, and 50 ml of methanol are refluxed for 2 hours. After stirring overnight at room temperature, the product crystallizes out, is filtered off and digested with 50 ml hot methanol to yield the title compound, 2.77 g, m.p. 228°-235°(d).

Aufarbeitung

  1. temperatureAfter refluxing for 5 minutes
  2. customThe reaction mixture is reduced to one-half volume by evaporation
  3. extractionextracted with chloroform (X 5)
  4. dry with materialThe chloroform washings are dried (Na2SO4)
  5. customevaporated
  6. customthe product crystallizes out
  7. filtrationis filtered off

Quellen und Nachweise

ORD-Eintrag
ord-c8cae7a0ec284539bbfdbfaaf55236d5
Quelldatensatz
uspto-grants-1979_05
Patentnummer
US04154846

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