Diisoamylamine → 3-fluoro-N,N-bis(3-methylbutyl)-4-nitrobenzamide

HRID 1160987

Reaktionsgleichung

Reaktionsgleichung von HRID 1160987
Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[F:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][C:32]=1[N+:33]([O-:35])=[O:34])[C:27]([OH:29])=O.[CH2:36]([NH:41][CH2:42][CH2:43][CH:44]([CH3:46])[CH3:45])[CH2:37][CH:38]([CH3:40])[CH3:39]>C(Cl)(Cl)Cl.C1COCC1>[F:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][C:32]=1[N+:33]([O-:35])=[O:34])[C:27]([N:41]([CH2:42][CH2:43][CH:44]([CH3:46])[CH3:45])[CH2:36][CH2:37][CH:38]([CH3:39])[CH3:40])=[O:29]

Komponenten

7

Edukt 4

HCID 10988DiisoamylamineHCID 757711-HydroxybenzotriazoleHCID 2306533-Fluoro-4-nitrobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 684471113-fluoro-N,N-bis(3-methylbutyl)-4-nitrobenzamideAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) (4.4 g, 1.1 eq) in solution in chloroform (25 ml) and 1-hydroxybenzotriazole (HOBt) (3.05 g, 1.1 eq) in solution in THF (40 ml) are added successively to 3-fluoro-4-nitrobenzoic acid (3.8 g, 1 eq) in solution in anhydrous THF (30 ml). The mixture is stirred for 1 hour at a temperature of approximately 20° C. then diisoamylamine (3.6 g, 1.1 eq) in solution in THF (30 ml) is added. After stirring for 16 hours at a temperature of approximately 20° C., the reaction mixture is concentrated under reduced pressure at 40° C. The residue is taken up in dichloromethane (200 ml) and water (70 ml). After decantation and extractions, the combined organic phases are washed with salt water, dried over Na2SO4 then concentrated under reduced pressure at 40° C. Purification of the compound by flash chromatography on silica gel (eluent: heptane/ethyl acetate 9:1) produces the expected compound in the form of a yellow oil (4.3 g; 65% yield).

Aufarbeitung

  1. stirringAfter stirring for 16 hours at a temperature of approximately 20° C.
  2. concentrationthe reaction mixture is concentrated under reduced pressure at 40° C
  3. extractionAfter decantation and extractions
  4. washthe combined organic phases are washed with salt water
  5. dry with materialdried over Na2SO4
  6. concentrationthen concentrated under reduced pressure at 40° C
  7. customPurification of the compound by flash chromatography on silica gel (eluent: heptane/ethyl acetate 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-52ce3ab13dc54d8184074ecacb33baab
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07816539B2

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