Acetyl chloride → N'-acetyl-2,2-dimethylpropanohydrazide

HRID 448026

Reaktionsgleichung

Reaktionsgleichung von HRID 448026
[CH3:1][C:2]([CH3:8])([CH3:7])[C:3]([NH:5][NH2:6])=[O:4].C(=O)(O)[O-].[Na+].[C:14](Cl)(=[O:16])[CH3:15]>O1CCCC1.O>[C:14]([NH:6][NH:5][C:3](=[O:4])[C:2]([CH3:8])([CH3:7])[CH3:1])(=[O:16])[CH3:15]

Komponenten

6

Edukt 3

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 5451472,2-Dimethylpropanehydrazide

Produkt 1

HCID 23525705N'-acetyl-2,2-dimethylpropanohydrazide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of 2,2-dimethyl-propionic acid hydrazide (2.32 g, 20 mmol), sodium bicarbonate (1.68 g, 20 mmol) in tetrahydrofuran and water (1:1, 40 mL) was added acetyl chloride (1.56 g, 20 mmol) dropwise. The mixture was stirred overnight and concentrated in vacuo. The residue was extracted with dichloromethane and isopropyl alcohol (10:1) (3×10 mL). The organic extracts were combined, dried over MgSO4 and concentrated to give a white solid. The solid was recrystallized from tetrahydrofuran and hexane (1:8) to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.11-1.14 (m, 9 H) 1.83 (s, 3 H) 9.28 (br s, 1 H) 9.53 (br s, 1 H); MS (ESI) m/z 159 (M+H)+.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. extractionThe residue was extracted with dichloromethane and isopropyl alcohol (10:1) (3×10 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customto give a white solid
  6. customThe solid was recrystallized from tetrahydrofuran and hexane (1:8)

Quellen und Nachweise

ORD-Eintrag
ord-66bee90cb8ed40fa841c72b09adb1271
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481574B2

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