Triethylamine → 3-(4-Chloro-butanoylamino)-5-methylsulfanyl-benzoic acid methyl ester

HRID 852555Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 852555
Cl.[CH3:2][O:3][C:4](=[O:14])[C:5]1[CH:10]=[C:9]([S:11][CH3:12])[CH:8]=[C:7]([NH2:13])[CH:6]=1.CCN(CC)CC.[Cl:22][CH2:23][CH2:24][CH2:25][C:26](Cl)=[O:27]>C(Cl)Cl.CCOC(C)=O>[CH3:2][O:3][C:4](=[O:14])[C:5]1[CH:10]=[C:9]([S:11][CH3:12])[CH:8]=[C:7]([NH:13][C:26](=[O:27])[CH2:25][CH2:24][CH2:23][Cl:22])[CH:6]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 783704-Chlorobutyryl chlorideHCID 693575963-Amino-5-methylsulfanyl-benzoic acid methyl ester hydrochloride

Produkt 1

HCID 693577003-(4-Chloro-butanoylamino)-5-methylsulfanyl-benzoic acid methyl esterAusbeute 103,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 3-amino-5-methylsulfanyl-benzoic acid methyl ester hydrochloride (D62) (0.13 g, 0.556 mmol, 1 equiv) in dry CH2Cl2 (2 ml) at 0° C. was added NEt3 (193 ml, 1.39 mmol, 2.5 equiv) then 4-chlorobutyryl chloride (69 ml, 0.612 mmol, 1.1 equiv), dropwise, over 2 min. The resulting solution was stirred at 0° C. for 15 min then at room temperature for 30 min. The solution was then diluted with AcOEt, washed sequentially with 2N aqueous HCl solution, saturated aqueous NaHCO3 solution and brine, dried over Na2SO4 and concentrated in vacuo to give 3-(4-chloro-butanoylamino)-5-methylsulfanyl-benzoic acid methyl ester (D64) (173 mg, 103%) as pale yellow crystals. [M+H]+=302.0, RT=3.20 min

Aufarbeitung

  1. waitat room temperature for 30 min
  2. washwashed sequentially with 2N aqueous HCl solution, saturated aqueous NaHCO3 solution and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6ed46d440efe4513ae9c5a11f1d3fda9
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07253198B2

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