ChemicalBook CAS DataBase List 4-METHYLACETANILIDE

4-METHYLACETANILIDE synthesis

10synthesis methods

Product Name:4-METHYLACETANILIDE
CAS Number:5602-96-0
Molecular formula:C9H11NO2
Molecular Weight:165.19

67-56-1 Synthesis

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619-55-6
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5602-96-0
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Yield:5602-96-0 97%

Reaction Conditions:

with dibromamine-T;1,8-diazabicyclo[5.4.0]undec-7-ene for 0.333333 h;Reflux;Hofmann rearrangement;

Steps:

Experimental procedure for the synthesis of carbamate:

General procedure: To a solution of amide (1 mmol) in methanol (10 mL) was added DBU (0.5 mL). To this solution TsNBr₂ (1 mmol) was added. The reaction mixture was heated under reflux condition for a period of 10-20 min (TLC). After completion of the reaction (TLC) methanol was evaporated under reduced pressure. The crude mixture was then dissolved in EtOAc. This solution was washed with 5% HCl and then with saturated Na₂CO₃ solution. The organic extracts were separated and dried over anhydrous Na₂SO₄. The crude product was purified by flash column chromatography using petroleum ether and ethyl acetate (4:1) as eluent to get the pure carbamate product.

References:

Borah, Arun Jyoti;Phukan, Prodeep [Tetrahedron Letters,2012,vol. 53,# 24,p. 3035 - 3037] Location in patent:experimental part

67-56-1 Synthesis

67-56-1
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201230-82-2 Synthesis