1,2-Dichloroethane → HCID 22328602, Verbindung

HRID 586130

Reaktionsgleichung

Reaktionsgleichung von HRID 586130
[CH2:1]([NH:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)[CH3:2].[OH:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[C:15]=1[C:16](O)=[O:17].C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C.CCOC(C)=O>[CH2:1]([N:3]([CH2:4][C:5]1[CH:6]=[CH:7][C:8]([O:11][CH3:12])=[CH:9][CH:10]=1)[C:16](=[O:17])[C:15]1[C:14]([OH:13])=[CH:22][CH:21]=[CH:20][C:19]=1[OH:23])[CH3:2]

Komponenten

7

Edukt 4

HCID 111,2-DichloroethaneHCID 93382,6-Dihydroxybenzoic AcidHCID 181649HOAtHCID 296018Benzenemethanamine, N-ethyl-4-methoxy-

Produkt 1

HCID 22328602HCID 22328602, VerbindungAusbeute 32,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of N-ethyl-4-methoxybenzyl amine (1.07 g, 6.49 mmol) in DMF (10 mL) was added 2,6-dihydroxybenzoic acid (1.0 g, 6.49 mmol) followed by HOAt (0.97 g, 7.14 mmol) and EDC (1.31 g, 6.81 mmol). After stirring overnight, the reaction was diluted with EtOAc prior to washing 3× with H2O. The combined aqueous layers were extracted once with EtOAc. The organic fractions were combined, washed once with brine, and dried over Na2SO4 prior to concentrating using a rotary evaporator. The residue was chromatographed on silica gel using 75% EtOAc/hexane as the eluent. The resulting promising impure fractions were further purified by silica gel chromatography. A total of 631 mg of the desired N-ethyl-N-4-methoxybenzyl 2,6-dihydroxybenzamide was obtained.

Aufarbeitung

  1. washto washing 3× with H2O
  2. extractionThe combined aqueous layers were extracted once with EtOAc
  3. washwashed once with brine
  4. dry with materialdried over Na2SO4
  5. concentrationto concentrating
  6. customa rotary evaporator
  7. customThe residue was chromatographed on silica gel using 75% EtOAc/hexane as the eluent
  8. customThe resulting promising impure fractions were further purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5e527322bbd34ff1bd7734ab74b1d29f
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06936590B2

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