1,2-Dichloroethane → 2-Methoxy-4-methylbenzamide

HRID 1518590Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1518590
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:4]=1[C:5](O)=[O:6].C(Cl)CCl.C1C=CC2N(O)N=[N:23]C=2C=1.N>ClCCl>[CH3:1][O:2][C:3]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:4]=1[C:5]([NH2:23])=[O:6]

Komponenten

6

Edukt 4

HCID 111,2-DichloroethaneHCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 5971642-Methoxy-4-methylbenzoic acid

Produkt 1

HCID 219473972-Methoxy-4-methylbenzamideAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of 2-methoxy-4-methylbenzoic acid (20 g, 120.4 mmol), EDC (23.1 g, 120.4 mmol) and HOBt (16.3 g, 120.4 mmol) in dichloromethane (1 L) was added NH3 (7N in MeOH, 52 mL, 3 eq) dropwise. The reaction mixture was stirred at room temperature overnight then washed successively with HCl (1N), saturated aq.NaHCO3, water and brine, dried over MgSO4, filtered and evaporated. The residue was recrystallized from ethyl acetate/hexane to give 16.5 gr of 2-methoxy-4-methylbenzamide (83% yield).

Aufarbeitung

  1. washthen washed successively with HCl (1N)
  2. dry with materialNaHCO3, water and brine, dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was recrystallized from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-684e4b93eb264e9eb912c3a906b4b0a4
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09072313B2

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