Triethylamine → 3-(N,N-Diethylaminosulfonyl)-N-methoxy-N-methylbenzamide

HRID 2300766

Reaktionsgleichung

Reaktionsgleichung von HRID 2300766
[CH2:1]([N:3]([CH2:16][CH3:17])[S:4]([C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10](O)=[O:11])(=[O:6])=[O:5])[CH3:2].Cl.[CH3:19][NH:20][O:21][CH3:22].C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC.C([O-])(O)=O.[Na+]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:1]([N:3]([CH2:16][CH3:17])[S:4]([C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([N:20]([O:21][CH3:22])[CH3:19])=[O:11])(=[O:6])=[O:5])[CH3:2]

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 516892Sodium BicarbonateHCID 7945953-(Diethylsulfamoyl)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 183755293-(N,N-Diethylaminosulfonyl)-N-methoxy-N-methylbenzamideAusbeute 38,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3-(N,N-diethylaminosulfonyl)benzoic acid (1.17 g, 4.55 mmol) and N,O-dimethylhydroxylamine hydrochloride (498 mg, 5.11 mmol) were dissolved in CH2Cl2 (30 mL). To this solution was added triethylamine (1.9 mL, 14 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (970 mg, 5.06 mmol) and 4-(N,N-dimethylamino)pyridine (117 mg, 0.958 mmol). The resulting solution was stirred at room temperature for 17 h then poured into saturated aqueous NaHCO3 and extracted 3× with ethyl acetate. The combined organics were washed with brine then dried over MgSO4 and concentrated under reduced pressure. The residue was purified by column chromatography (silica, 70:30 hexanes:acetone) to yield 522 mg of the title compound.

Aufarbeitung

  1. extractionextracted 3× with ethyl acetate
  2. washThe combined organics were washed with brine
  3. dry with materialthen dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (silica, 70:30 hexanes:acetone)

Quellen und Nachweise

ORD-Eintrag
ord-d58cab61ebb845fb8c8419a52f6cd322
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06498165B1

Verknüpfte Notizen

Wird geladen…