Water → Methyl 4-[3-(2-chloro-ethoxy)-propionyl-amino]-3-methyl-benzoate

HRID 551233

Reaktionsgleichung

Reaktionsgleichung von HRID 551233
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH3:12].C(N(CC)CC)C.[Cl:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][C:26](Cl)=[O:27].O>C1COCC1>[Cl:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][C:26]([NH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH3:12])=[O:27]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 2736799Methyl 4-amino-3-methylbenzoateHCID 860693723-(2-Chloroethoxy)propanoyl chloride

Produkt 1

HCID 67048278Methyl 4-[3-(2-chloro-ethoxy)-propionyl-amino]-3-methyl-benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

1.70 g (10.3 mmol) methyl 4-amino-3-methyl-benzoate in 10 ml THF are combined with 2.84 ml (20.6 mmol) triethylamine and stirred for 20 minutes at ambient temperature. Then a solution of 1.78 g (10.4 mmol) 3-(2-chloro-ethoxy)-propionic acid-chloride in 25 ml THF is added dropwise and the mixture is stirred for a further 2.5 hours at ambient temperature. Then water is added and the mixture is extracted with ethyl acetate. The combined organic phases are dried over sodium sulphate and evaporated down completely i. vac. The residue is purified by chromatography on silica gel (eluting gradient: petroleum ether/ethyl acetate=7:3→6:4).

Aufarbeitung

  1. stirringthe mixture is stirred for a further 2.5 hours at ambient temperature
  2. extractionthe mixture is extracted with ethyl acetate
  3. dry with materialThe combined organic phases are dried over sodium sulphate
  4. customevaporated down completely
  5. customThe residue is purified by chromatography on silica gel (eluting gradient: petroleum ether/ethyl acetate=7:3→6:4)

Quellen und Nachweise

ORD-Eintrag
ord-9512c293d977477c9bf46f8f1dc169d9
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947700B2

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