Triethylamine → HCID 70980720, Verbindung

HRID 1749078Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1749078
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][O:6][C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[C:9](Cl)[N:8]=1)[CH3:2].C(N(CC)CC)C.[CH3:25][O:26][C:27]1[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[CH:31][C:28]=1[CH2:29][NH2:30]>CC#N>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][O:6][C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[C:9]([NH:30][CH2:29][C:28]2[CH:31]=[CH:32][C:33]([O:35][CH3:36])=[CH:34][C:27]=2[O:26][CH3:25])[N:8]=1)[CH3:2]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 5972502,4-DimethoxybenzylamineHCID 13245756Ethyl 2-[(6-chloro-3-nitro-2-pyridinyl)oxy]acetate

Produkt 1

HCID 70980720HCID 70980720, VerbindungAusbeute 79,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a cooled (˜10° C.) solution of (6-chloro-3-nitro-pyridin-2-yloxy)-acetic acid ethyl ester (8.0 g, 30.8 mmol) in MeCN (80 mL) was added a solution of triethylamine (6.4 mL, 46 mmol) and 2,4-dimethoxybenzylamine (5.5 mL, 37 mmol). The mixture was then stirred for 16 hours at ambient temperature and then concentrated in vacuo. The residue was partitioned between EtOAc and aqueous potassium hydrogenphosphate solution. The EtOAc layer was then washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified using SiO2 chromatography (10-50% EtOAc/Petrol) to give [6-(2,4-dimethoxy-benzylamino)-3-nitro-pyridin-2-yloxy]acetic acid ethyl ester (9.53 g) as a yellow solid. MS: [M+H]+ 392

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between EtOAc and aqueous potassium hydrogenphosphate solution
  3. washThe EtOAc layer was then washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-e92a3be54b6d4d42b4c82659aa8857bc
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09155743B2

Notizen zur Reaktion

Wird geladen…