Hydrochloric Acid → HCID 69300805, Verbindung

HRID 131285Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 131285
[CH2:1]([NH:8][C:9]1[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:20][CH2:21][CH2:22][CH2:23][C:24](Cl)=[O:25].C(N(CC)C(C)C)(C)C.Cl>C(Cl)Cl.C(Cl)(Cl)Cl>[CH2:1]([N:8]([C:9]1[CH:10]=[CH:11][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:18][CH:19]=1)[C:24](=[O:25])[CH2:23][CH2:22][CH2:21][Cl:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 783704-Chlorobutyryl chlorideHCID 81531DiisopropylethylamineHCID 3832836Ethyl 4-(benzylamino)benzoate

Produkt 1

HCID 69300805HCID 69300805, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of ethyl 4-benzylaminobenzoate (6.0 g) in methylene chloride (60 mL) is added dropwise chlorobutyryl chloride (3.95 mL) and N,N-diisopropylethylamine (6.14 mL) under ice-cooling, and the mixture is stirred for 12 hours. The reaction mixture is diluted with chloroform and thereto is added 10% HCl. The organic layer is separated, washed successively with water, a saturated sodium hydrogencarbonate solution, water, and saturated brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue is purified by flash column chromatography on silica gel (Solvent; n-hexane:ethyl acetate=4:1) to give ethyl 4-[N-benzyl-N-(4-chlorobutyryl)amino]benzoate (8.27 g, yield; quantitative) as an oil. MS (APCI) m/z; 360/362 [M+H]+

Aufarbeitung

  1. temperaturecooling
  2. customThe organic layer is separated
  3. washwashed successively with water
  4. dry with materiala saturated sodium hydrogencarbonate solution, water, and saturated brine, dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by flash column chromatography on silica gel (Solvent; n-hexane:ethyl acetate=4:1)

Quellen und Nachweise

ORD-Eintrag
ord-3a129cab96f347c082e7fba86edc7c97
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384952B2

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