4-Methylmorpholine → HCID 86607991, Verbindung

HRID 558480Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 558480
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[C:13]([F:16])([F:15])[F:14])[C:7]([OH:9])=O)[CH3:2].Cl.[CH3:18][NH:19][O:20][CH3:21].CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>CN(C1C=CN=CC=1)C.C(Cl)Cl.CN(C=O)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[C:13]([F:16])([F:15])[F:14])[C:7]([N:19]([O:20][CH3:21])[CH3:18])=[O:9])[CH3:2]

Komponenten

8

Edukt 4

HCID 79724-MethylmorpholineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 670005513-Ethoxy-4-(trifluoromethyl)benzoic acid

Produkt 1

HCID 86607991HCID 86607991, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

To a mixture of 3-ethoxy-4-trifluoromethyl-benzoic acid from step 6 (13.76 g, 59 mmol), N,O-dimethylhydroxylamine hydrochloride (9.17 g, 94 mmol), N-methylmorpholine (9.51 mL, 94 mmol) and 4-DMAP (718 mg, 6 mmol) in DCM (185 mL) and DMF (38 mL) at 0° C. was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) (13.52 g, 70 mmol), and the mixture was stirred at 23° C. for 18 h. Poured onto ice cold 1 N HCl, extracted with TBME, washed with sat. NaHCO3-sol. and brine, dried over Na2SO4. Removal of the solvent in vacuum left the title compound as a light brown oil (16.15 g, 100%, which was used without further purification. MS (ISP) 278.4 [M+H].

Aufarbeitung

  1. additionPoured onto ice cold 1 N HCl
  2. extractionextracted with TBME
  3. washwashed with sat. NaHCO3-sol
  4. dry with materialand brine, dried over Na2SO4
  5. customRemoval of the solvent in vacuum
  6. waitleft the title compound as a light brown oil (16.15 g, 100%, which
  7. customwas used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-9a2a1b0c9c3c43eca6c336ebaf55023e
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063048B2

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