Hydrochloric Acid → HCID 178468758, Verbindung

HRID 505910

Reaktionsgleichung

Reaktionsgleichung von HRID 505910
[NH2:1][C:2]1[C:12]([NH2:13])=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[N+:14]([C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=1)([O-:16])=[O:15].Cl.O.[S-2].[Na+].[Na+]>CO.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C(O)(=O)C>[N+:14]([C:17]1[CH:24]=[CH:23][C:20]([C:21]2[NH:1][C:2]3[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:9][CH:10]=[CH:11][C:12]=3[N:13]=2)=[CH:19][CH:18]=1)([O-:16])=[O:15]

Komponenten

9

Edukt 4

HCID 313Hydrochloric AcidHCID 5414-NitrobenzaldehydeHCID 11171330Ethyl 2,3-diaminobenzoateHCID 19906495Sodium sulfide monohydrate

Produkt 1

HCID 178468758HCID 178468758, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 8895Cupric acetateKatalysatorHCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittel2×HCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

1.5 g (8.3 mmol) of ethyl 2,3-diaminobenzoate and 1.1 ml of concentrated acetic acid were dissolved in 50 ml of methanol. 1.6 g (10.8 mmol) of 4-nitrobenzaldehyde, dissolved in 150 ml of methanol, were then added dropwise over a period of 30 minutes. 2.2 g (10.8 mmol) of copper(II) acetate, dissolved in 100 ml of warm water, were then rapidly added dropwise, and the entire mixture was subsequently refluxed for 20 minutes. The reaction solution was cooled to 50° C. and 3 ml of 32% strength hydrochloric acid were added. This was followed by careful dropwise addition of a solution of 3.1 g of sodium sulfide hydrate in 50 ml of water, and the entire mixture was stirred for another 15 minutes. The reaction solution was poured into ice-water and the resulting precipitate was filtered off with suction. The filtrate was made alkaline using aqueous sodium bicarbonate solution and extracted repeatedly with ethyl acetate. The ethyl acetate phase was separated off, dried and concentrated under reduced pressure. This gave 2.2 g of the intermediate.

Aufarbeitung

  1. additionwere then added dropwise over a period of 30 minutes
  2. additionwere then rapidly added dropwise
  3. temperaturethe entire mixture was subsequently refluxed for 20 minutes
  4. filtrationthe resulting precipitate was filtered off with suction
  5. extractionextracted repeatedly with ethyl acetate
  6. customThe ethyl acetate phase was separated off
  7. customdried
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9b83b6de3022465da82d947610961d9c
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781596B1

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