Triethylamine → N-(3,4-diaminophenyl)-2-(diethylamino)acetamide

HRID 1091639

Reaktionsgleichung

Reaktionsgleichung von HRID 1091639
[N+:1]([C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=1[NH2:11])([O-])=O.[Na+].[CH2:13]([N:15]([CH2:20][CH3:21])[CH2:16][C:17]([O-])=[O:18])[CH3:14].CCOP(ON1N=NC2C=CC=CC=2C1=O)(OCC)=O.C(N(CC)CC)C>C(#N)C.C(O)C.[Pd]>[NH2:1][C:4]1[CH:9]=[C:8]([NH:10][C:17](=[O:18])[CH2:16][N:15]([CH2:20][CH3:21])[CH2:13][CH3:14])[CH:7]=[CH:6][C:5]=1[NH2:11]

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 42939953-(Diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-oneHCID 43383702-Nitro-4-phenylenediamineHCID 23670834Glycine, N,N-diethyl-, sodium salt (1:1)

Produkt 1

HCID 66593690N-(3,4-diaminophenyl)-2-(diethylamino)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

2-Nitrobenzene-1,4-diamine (1.55 g, 10.1 mmol), N,N-diethylglycine sodium salt (1.61 g, 10.6 mmol) and DEPBT (3.02 g, 10.0 mmol) were suspended in acetonitrile (75 mL). Triethylamine (2.8 mL, 20.0 mmol) was added and the solution stirred overnight at room temperature. The brown precipitate which was formed was filtered and discarded. The filtrate was concentrated and the residue partitioned between EA and saturated aqueous sodium bicarbonate. The organic phase was washed with water and then with brine, dried over sodium sulfate, and the solvent removed under reduced pressure. The residue was dissolved in ethanol (50 mL) and hydrogenated at atmospheric pressure with 10% palladium on charcoal (1.0 g, 0.9 mmol) at room temperature overnight. Filtration and concentration under reduced pressure gave N-(3,4-diaminophenyl)-2-(diethylamino)acetamide as a light brown semi-solid, which solidified and turned blue on standing.

Aufarbeitung

  1. customThe brown precipitate which was formed
  2. filtrationwas filtered
  3. concentrationThe filtrate was concentrated
  4. customthe residue partitioned between EA and saturated aqueous sodium bicarbonate
  5. washThe organic phase was washed with water
  6. dry with materialwith brine, dried over sodium sulfate
  7. customthe solvent removed under reduced pressure
  8. filtrationFiltration and concentration under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-bd23b24b0e704bdcb05f4b922f251601
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129396B2

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