Diisopropylethylamine → N-[2-(1,3-dimethylbutyl)phenyl]-2-iodothiophene-3-carboxamide

HRID 19963

Reaktionsgleichung

Reaktionsgleichung von HRID 19963
C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.[I:34][C:35]1[S:36][CH:37]=[CH:38][C:39]=1[C:40]([OH:42])=O.[CH3:43][CH:44]([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=1[NH2:55])[CH2:45][CH:46]([CH3:48])[CH3:47]>C(#N)C.O>[CH3:43][CH:44]([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=1[NH:55][C:40]([C:39]1[CH:38]=[CH:37][S:36][C:35]=1[I:34])=[O:42])[CH2:45][CH:46]([CH3:47])[CH3:48]

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 115284412-(1,3-Dimethylbutyl)anilineHCID 230940222-Iodothiophene-3-carboxylic acid

Produkt 1

HCID 11315926N-[2-(1,3-dimethylbutyl)phenyl]-2-iodothiophene-3-carboxamideAusbeute 21,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Under protective gas (argon), 0.56 ml (3.38 mmol) of N,N-diisopropylethylamine and 1.18 g (2.5 mmol) of bromotrispyrrolidinophosphonium hexafluorophosphate (PyBrop) are added to a solution of 516 mg (2.0 mmol) of 2-iodothiophene-3-carboxylic acid and 300 mg (1.7 mmol) of 2-(1,3-dimethylbutyl)phenylamine in 10 ml of acetonitrile. The reaction mixture is stirred at room temperature for 24 hours and, for work-up, added to water, extracted with ethyl acetate, dried over sodium sulphate and concentrated under reduced pressure. Column chromatography (cyclohexane/ethyl acetate gradient) gives 150 mg (21% of theory) of N-[2-(1,3-dimethylbutyl)phenyl]-2-iodothiophene-3-carboxamide [log P (pH 2.3)=4.14].

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-700d18bc9c354bc19c34272aa8316f70
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745483B2

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