4-Methyl-3-nitrobenzoic acid → (4-Ethylpiperazin-1-yl)-(4-methyl-3-nitrophenyl)methanone

HRID 912153

Reaktionsgleichung

Reaktionsgleichung von HRID 912153
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].C1C=CC2N(O)N=NC=2C=1.[CH2:24]([N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)[CH3:25]>ClCCl>[CH2:24]([N:26]1[CH2:31][CH2:30][N:29]([C:6]([C:5]2[CH:9]=[CH:10][C:2]([CH3:1])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=2)=[O:8])[CH2:28][CH2:27]1)[CH3:25]

Komponenten

5

Edukt 3

HCID 73194-Methyl-3-nitrobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 791961-Ethylpiperazine

Produkt 1

HCID 808340(4-Ethylpiperazin-1-yl)-(4-methyl-3-nitrophenyl)methanoneAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To 4-methyl-3-nitro-benzoic acid (730 mg, 4.03 mmol), WSCI (930 mg, 4.85 mmol), HOBt (110 mg, 0.674 mmol) and N-ethylpiperazine (608 μl, 4.79 mmol), dichloromethane (8 ml) was added, followed by stirring for 13 hours. The reaction mixture was washed with aqueous ammonium chloride solution, and subsequently dried over sodium sulfate. After filtering sodium sulfate, the filtrate was concentrated under reduced pressure, to obtain (4-ethyl-piperazin-1-yl)-(4-methyl-3-nitro-phenyl)-methanone (1.06 g, 95%).

Aufarbeitung

  1. washThe reaction mixture was washed with aqueous ammonium chloride solution
  2. dry with materialsubsequently dried over sodium sulfate
  3. filtrationAfter filtering sodium sulfate
  4. concentrationthe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8036c311c9f7474e8a9ec5c3ab79236f
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022205B2

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