Triethylamine → 3-Fluoro-4-(1-methylethoxy)-N-methoxy-N-methylbenzamide

HRID 1690165Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1690165
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH:12]([CH3:14])[CH3:13])[C:5]([OH:7])=O.Cl.[CH3:16][O:17]CN.CCN=C=NCCC[N:28]([CH3:30])C.Cl.C(N(CC)CC)C.C1C=CC2N(O)N=NC=2C=1.O>ClCCl.O>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH:12]([CH3:14])[CH3:13])[C:5]([N:28]([O:17][CH3:16])[CH3:30])=[O:7]

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 179028843-Fluoro-4-isopropoxybenzoic acidHCID 21959107Methoxymethanamine hydrochloride

Produkt 1

HCID 866394073-Fluoro-4-(1-methylethoxy)-N-methoxy-N-methylbenzamideAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3-Fluoro-4-(1-methylethoxy)benzoic acid (100 mg, 0.505 mmol) was dissolved in dichloromethane (2.5 mL). The resultant mixture was added with methoxymethylamine hydrochloride (99 mg, 1.01 mmol), WSC-HCl (106 mg, 0.555 mmol), triethylamine (422 μL, 3.03 mmol), and HOBt-H2O (34 mg, 0.252 mmol) sequentially, and stirred at room temperature overnight. The reaction solution was added with water and extracted with ethyl acetate. The organic layer was washed with 5% aqueous solution of hydrochloric acid, a saturated aqueous solution of sodium hydrogen carbonate and brine, dried using anhydrous sodium sulfate, and concentrated in vacuo. 3-Fluoro-4-(1-methylethoxy)-N-methoxy-N-methylbenzamide (117 mg, yield 96%) was obtained as a colorless oil.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with 5% aqueous solution of hydrochloric acid
  3. dry with materiala saturated aqueous solution of sodium hydrogen carbonate and brine, dried
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-196c43963c26432fb9a1622bf4430d6c
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153634B2

Notizen zur Reaktion

Wird geladen…