Water → N-(3-{[4-(difluoromethoxy)phenyl]ethynyl}phenyl)-2-methoxyacetamide

HRID 30559

Reaktionsgleichung

Reaktionsgleichung von HRID 30559
[F:1][CH:2]([F:19])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:13]=[C:14]([CH:16]=[CH:17][CH:18]=2)[NH2:15])=[CH:6][CH:5]=1.C(N(CC)CC)C.[CH3:27][O:28][CH2:29][C:30](Cl)=[O:31].O>C(Cl)Cl>[F:1][CH:2]([F:19])[O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]#[C:11][C:12]2[CH:13]=[C:14]([NH:15][C:30](=[O:31])[CH2:29][O:28][CH3:27])[CH:16]=[CH:17][CH:18]=2)=[CH:8][CH:9]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 96623Methoxyacetyl chlorideHCID 574358643-{[4-(Difluoromethoxy)phenyl]ethynyl}aniline

Produkt 1

HCID 59790309N-(3-{[4-(difluoromethoxy)phenyl]ethynyl}phenyl)-2-methoxyacetamideAusbeute 97,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A cold (0° C.) solution of 3-{[4-(difluoromethoxy)phenyl]ethynyl}aniline (1 g, 3.86 mmol), triethylamine (0.65 mL, 4.63 mmol) in CH2Cl2 was treated dropwise with methoxyacetyl chloride (0.5 g, 4.63 mmol), allowed to come to room temperature, stirred for 2 hours, poured into water and extracted with EtOAc/ethyl ether 1/1. The organic extracts were combined, dried over MgSO4 and concentrated in vacuo. Purification of the resultant residue on silica gel (Biotage) using hexanes/EtOAc (1/1) as the eluting solvent gave N-(3-{[4-(difluoromethoxy)phenyl]ethynyl}phenyl)-2-methoxyacetamide as a yellow solid (1.25 g, 94% yield), MS m/e (M+H)+ 332; 1H NMR (400 MHz, DMSO-d6) 3.30 (s, 3H), 3.97 (s, 2H), 7.2 (m, 3H), 7.3 (m, 2H), 7.6 (m, 3H), 7.9(t, J=1.7 Hz, 1H), 9.84 (s, 1H).

Aufarbeitung

  1. customto come to room temperature
  2. extractionextracted with EtOAc/ethyl ether 1/1
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customPurification of the resultant residue on silica gel (Biotage)

Quellen und Nachweise

ORD-Eintrag
ord-91311c9bbf924e4fa645869a80c7b2d3
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423158B2

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