1,2-Dichloroethane → 2',3'-Dimethyl-3-nitrobenzanilide

HRID 1780803

Reaktionsgleichung

Reaktionsgleichung von HRID 1780803
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=O)([O-:3])=[O:2].[CH3:13][C:14]1[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][C:15]=1[NH2:16].ON1C2C=CC=CC=2N=N1.C(Cl)CCl>CN(C=O)C.C(N(CC)CC)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([NH:16][C:15]1[CH:17]=[CH:18][CH:19]=[C:20]([CH3:21])[C:14]=1[CH3:13])=[O:9])([O-:3])=[O:2]

Komponenten

7

Edukt 4

HCID 111,2-DichloroethaneHCID 68932,3-DimethylanilineHCID 84973-Nitrobenzoic acidHCID 757711-Hydroxybenzotriazole

Produkt 1

HCID 8165712',3'-Dimethyl-3-nitrobenzanilide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution of 3-nitrobenzoic acid (3.0 g ) and 2,3-dimethylaniline (2.17 g) in 20 mL of DMF was added 1-hydroxybenzotriazole (2.75 g), EDC (3.44 g) and triethylamine (7.39 mL). The resulting solution was stirred for 16 h. The DMF was evaporated in vacuo and the residue was partitioned with ethyl acetate and water. The ethyl acetate layer was extracted w/50 mL each of 2% potassium hydrogen sulfate, saturated sodium bicarbonate, saturated sodium chloride, dried over magnesium sulfate and concentrated in vacuo to afford the title compound as a solid. NMR (300 MHz, CDCl3) δ 8.72 (1H, s), 8.40 (1 H, d, J=6 Hz), 8.26 (1H, d, J=9 Hz), 7.93 (IH, s), 7.69 (1H, t, J=9 Hz), 7.45 (1 H,d, J=9 Hz), 7.14 (1H, t, J=8 Hz), 7.08 (1H, d, J=9 Hz), 2.32 (3H, s), 2.21 (3H, s).

Aufarbeitung

  1. customThe DMF was evaporated in vacuo
  2. customthe residue was partitioned with ethyl acetate and water
  3. extractionThe ethyl acetate layer was extracted w/50 mL each of 2% potassium hydrogen sulfate, saturated sodium bicarbonate, saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4a7c0436fc1c4910b757badd95221d5b
Quelldatensatz
uspto-grants-1997_05
Patentnummer
US05631280

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