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2,2,2-Trifluoroethylamine hydrochloride → 3-azido-3-methyl-N-(2,2,2-trifluoroethyl)butanamide

HRID 2061093
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2061093
Cl.[F:2][C:3]([F:7])([F:6])[CH2:4][NH2:5].CCN(C(C)C)C(C)C.[N:17]([C:20]([CH3:26])([CH3:25])[CH2:21][C:22](Cl)=[O:23])=[N+:18]=[N-:19]>ClCCCl>[N:17]([C:20]([CH3:26])([CH3:25])[CH2:21][C:22]([NH:5][CH2:4][C:3]([F:7])([F:6])[F:2])=[O:23])=[N+:18]=[N-:19]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 97722,2,2-Trifluoroethylamine hydrochlorideHCID 81531DiisopropylethylamineHCID 601345073-Azido-3-methylbutanoyl chloride

Produkt 1

HCID 601345313-azido-3-methyl-N-(2,2,2-trifluoroethyl)butanamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

To a stirred ice cold solution of 2,2,2-trifluoroethanamine hydrochloride (7.10 g, 1 equiv, 52.4 mmol) and DIEA (18.0 mL, 2.0 equiv, 0.103 mol) in anhydrous DCE (150 mL) was added 3-azido-3-methylbutanoyl chloride (8.46 g, 52.4 mmol) in small portions. The ice bath was removed and the reaction was stirred and left at room temperature for 3 h. Water (150 mL) was added to the reaction mixture and the contents poured into a separatory funnel. The organic layer was separated and washed with 1 M HCl (2×150 mL) and brine (150 mL). It was dried over anhydrous MgSO4, filtered, concentrated and dried under high vacuum to give a crude oil (10.9 g, 94.4). This material was used without further purification. 1H NMR (CDCl3, 400 MHz): δ 1.42 (s, 6H), 2.40 (s, 2H), (dq, J=2.4 & 8.8, 2H). LRMS (ESI+) for C7H11F3N4O (224.1); Found: 225 (MH+).

Aufarbeitung

  1. customThe ice bath was removed
  2. additionWater (150 mL) was added to the reaction mixture
  3. additionthe contents poured into a separatory funnel
  4. customThe organic layer was separated
  5. washwashed with 1 M HCl (2×150 mL) and brine (150 mL)
  6. dry with materialIt was dried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customdried under high vacuum
  10. customto give a crude oil (10.9 g, 94.4)
  11. customThis material was used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-c181259ff82d460293278ed085719e36
Quelldatensatz
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08278482B2

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