ChemicalBook CAS DataBase List tert-Butyl carbazate

tert-Butyl carbazate synthesis

11synthesis methods

Product Name:tert-Butyl carbazate
CAS Number:870-46-2
Molecular formula:C5H12N2O2
Molecular Weight:132.16

24424-99-5

870-46-2

General procedure for the synthesis of tert-butyl hydrazinecarboxylate from di-tert-butyl dicarbonate: Hydrazine hydrate (113 mg, 2.26 mmol, 2.26 eq.) was dissolved in isopropanol (IPA, 5 mL) and the solution was cooled to 0 °C. Subsequently, di-tert-butyl dicarbonate (174 mg, 1 mmol, 1 eq.) dissolved in isopropanol (IPA, 1 mL) was added dropwise. The reaction mixture was stirred at 0 °C for 2 hours. After completion of the reaction, the solvent was removed by rotary evaporator. The residue was dissolved in dichloromethane (DCM) and dried with anhydrous magnesium sulfate (MgSO4). After drying, the desiccant was removed by filtration and the solvent was again removed by rotary evaporator to give tert-butylhydrazine carboxylate (10) as a white semi-solid (128 mg, 97% yield). The product was confirmed by nuclear magnetic resonance hydrogen spectrum (1H NMR, 300 MHz, CDCl3): δ 6.73 (s, 1H), 3.83 (s, 2H), 1.46 (s, 9H); nuclear magnetic resonance carbon spectrum (13C NMR, 75 MHz, CDCl3): δ 158.2, 80.1, 28.2.

24424-99-5 Synthesis

24424-99-5
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$13.50/25G

870-46-2
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$5.00/10g

Yield:870-46-2 97%

Reaction Conditions:

with hydrazine hydrate in isopropyl alcohol at 0; for 2 h;

Steps:

Preparation of tert-butyl hydrazinecarboxylate 10:

Hydrazine hydrate (113 mg, 2.26 mmol, 2.26 equiv) was dissolved in IPA (5 mL) and cooled down to 0 °C. Di-tert-butyl carbonate (174 mg, 1 mmol, 1 equiv) in IPA (1 mL) was added drop-wise and the mixture was stirred for 2 h. The solvent was then evaporated and the residue was dissolved in DCM, dried over MgSO₄, and filtered. Evaporation of the solvent gave tert-butyl hydrazinecarboxylate 10 as a white semi-solid (128 mg, 97%). ¹H NMR (300 MHz, CDCl₃) δ 6.73(s, 1H), 3.83 (s, 2H), 1.46 (s, 9H); ¹³C NMR (75 MHz, CDCl₃) δ 158.2, 80.1, 28.2.²¹

References:

Vertesaljai, Peter;Lebedyeva, Iryna O.;Oliferenko, Alexander A.;Qi, Xin;Fu, Junjie;Ostrov, David A.;Asiri, Abdullah M.;Dennis Hall;Katritzky, Alan [Tetrahedron Letters,2015,vol. 56,# 48,p. 6653 - 6655]

6627-89-0 Synthesis