Hydrochloric Acid → N-Methoxy-N-methyl-3-(2-ethylbutyl)cyclobutanecarboxamide

HRID 1912091Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1912091
[CH2:1]([CH:3]([CH2:12][CH3:13])[CH2:4][CH:5]1[CH2:8][CH:7]([C:9](O)=[O:10])[CH2:6]1)[CH3:2].Cl.[CH3:15][NH:16][O:17][CH3:18].C(N(CC)C(C)C)(C)C.CCN=C=NCCCN(C)C.Cl.Cl>CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl>[CH3:18][O:17][N:16]([CH3:15])[C:9]([CH:7]1[CH2:8][CH:5]([CH2:4][CH:3]([CH2:12][CH3:13])[CH2:1][CH3:2])[CH2:6]1)=[O:10]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 866750493-(2-Ethylbutyl)cyclobutanecarboxylic acid

Produkt 1

HCID 86675050N-Methoxy-N-methyl-3-(2-ethylbutyl)cyclobutanecarboxamideAusbeute 107 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

3-(2-Ethylbutyl)cyclobutanecarboxylic acid (10.0 g) and chloroform (100 mL) were mixed. To the mixture were added N,O-dimethylhydroxylamine hydrochloride (6.36 g), N,N-diisopropylethylamine (11.3 mL), WSC.HCl (12.5 g) and 4-dimethylaminopyridine (7.96 g) at ice temperature. The mixture was stirred at RT overnight. After an addition of 6 N hydrochloric acid (40 mL) at ice temperature, the aqueous layer was removed. The organic layer was washed with 1 N hydrochloric acid (50 mL), water (50 mL), saturated aqueous sodium bicarbonate (50 mL) and brine (50 mL), then dried over sodium sulfate. The sodium sulfate was filtered off and the filtrate was concentrated in vacuo to give the title compound (13.2 g) as a crude product.

Aufarbeitung

  1. customthe aqueous layer was removed
  2. washThe organic layer was washed with 1 N hydrochloric acid (50 mL), water (50 mL), saturated aqueous sodium bicarbonate (50 mL) and brine (50 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationThe sodium sulfate was filtered off
  5. concentrationthe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-06a73f76efc64c5897f8c35ca8c88d11
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08604069B2

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