tert-butyl methyl-(4-nitrophenyl)carbamate synthesis

5synthesis methods

Product Name:tert-butyl methyl-(4-nitrophenyl)carbamate
CAS Number:474020-88-7
Molecular formula:C12H16N2O4
Molecular Weight:252.27

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tert-butyl methyl-(4-nitrophenyl)carbamate

474020-88-7
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Yield:474020-88-7 300 mg

Reaction Conditions:

Stage #1: tert-butyl N-(4-nitrophenyl)carbamatewith sodium hydride in tetrahydrofuran;paraffin oil at 0; for 0.5 h;
Stage #2: methyl iodide in tetrahydrofuran;paraffin oil at 20 - 50; for 16 h;

Steps:

12 Tert-butyl N-methyl-N-(4-nitrophenyl)carbamate

Tert-butyl N-methyl-N-(4-nitrophenyl)carbamate
To a stirred solution of NaH (60% dispersion in paraffin oil) (251 mg, 6.28 mmol) in THF (6.0 mL) at 0° C. was added a solution of tert-butyl N-(4-nitrophenyl)carbamate (1.0 g, 4.19 mmol) in THF (4.0 mL) over a period of 15 min.
The reaction mixture was stirred at this temperature for 15 min and to it was added methyl iodide (590.8 mg, 4.19 mmol).
The reaction mixture was warmed to rt, and was stirred at 50° C. for 16 h.
The mixture was cooled, was quenched with ice cold water (10.0 mL), and was extracted with EtOAc (3*50 mL).
The combined EtOAc extract was washed with water (50 mL), saturated aqueous NaCl (50 mL), dried over Na₂SO₄ and concentrated and reduced pressure.
The residue was further purified by column chromatography (SiO₂, 60-120, hexane/ethylacetete 90/10) to give the title compound (300 mg) as a yellow solid.

References:

US2017/174691,2017,A1 Location in patent:Paragraph 0774; 0775

24424-99-5 Synthesis