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ChemicalBook CAS DataBase List 4-METHYLACETANILIDE
5602-96-0

4-METHYLACETANILIDE synthesis

10synthesis methods
-

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

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