Pivaloyl chloride → N-(2-amino-4-chloro-5-nitrobenzyl)pivalamide

HRID 508871Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 508871
[NH2:1][CH2:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:6]([Cl:12])=[CH:5][C:4]=1[NH2:13].[C:14](Cl)(=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16]>C1COCC1>[NH2:13][C:4]1[CH:5]=[C:6]([Cl:12])[C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:3]=1[CH2:2][NH:1][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16]

Komponenten

4

Edukt 2

HCID 62493Pivaloyl chlorideHCID 900190742-(Aminomethyl)-5-chloro-4-nitrobenzenamine

Produkt 1

HCID 90018960N-(2-amino-4-chloro-5-nitrobenzyl)pivalamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-(aminomethyl)-5-chloro-4-nitrobenzenamine (2.5 g, 12.25 mmol) in THF (35 mL), TEA (3.0 mL) and pivaloyl chloride (1.96 mL, 14.7 mmol) were added and the reaction mass was stirred at RT for 5 h. The reaction mass was quenched with water and extracted with ethyl acetate. The organic layer was washed with dilute HCl and dilute sodium bicarbonate solution, separated, dried over anhydrous sodium sulphate and concentrated to afford 2.0 of the desired product. 1H NMR (300 MHz, DMSO d6): δ 1.12 (s, 9H), 4.30 (d, J=5.4 Hz, 2H), 7.81 (d, J=9.9 Hz, 1H), 7.96 (d, J=6.3 Hz, 1H), 8.21 (m, 1H).

Aufarbeitung

  1. customThe reaction mass was quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with dilute HCl and dilute sodium bicarbonate solution
  4. customseparated
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3412131dc5574650a0e910aa653bea1c
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096545B2

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