N-(4-aminophenyl)-N-methylmethanesulfonamide synthesis

5synthesis methods

Product Name:N-(4-aminophenyl)-N-methylmethanesulfonamide
CAS Number:251552-20-2
Molecular formula:C8H12N2O2S
Molecular Weight:200.26

512-56-1 Synthesis

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N-(4-aminophenyl)-N-methylmethanesulfonamide

251552-20-2
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Yield:251552-20-2 89%

Reaction Conditions:

with calcium hydroxide in N,N-dimethyl-formamide at 80; for 1 h;Sealed tube;

Steps:

General Methylation Procedure A (DMF Conditions)

General procedure: A 10-mL glass reaction tube fitted with a resealable Teflon valve wasequipped with a magnetic stir bar and charged with the heteroatomnucleophile substrate (1.0 mmol, 1.0 equiv), Ca(OH)2 (100 mg, 1.35mmol, 1.35 equiv), TMP (0.20 mL, 1.7 mmol, 1.7 equiv), and DMF (1.0mL). The flask was sealed and stirred at 80 °C (or at RT for some thiolsubstrates) until TLC indicated complete conversion. The reaction wasthen worked up as described below. Workup Procedure A After complete conversion, 1 N HCl (5 mL) was added and the mixturewas extracted with CH2Cl2 (10 mL). The organic phase was separated,washed with H2O (20 mL), dried over Na2SO4, filtered, and then concentratedin vacuo. The resulting residue was purified by silica gelcolumn chromatography to afford the desired methylated product.Workup Procedure B After complete conversion, petroleum ether (5 mL) was added, andthe solid was smashed into fine particles using a spatula and sonicatedfor 5 min. The resulting residue was then directly subjected to silicagel column chromatography to afford the desired methylated product.Workup Procedure C After complete conversion, CH2Cl2 (5 mL) was added, and the mixturewas filtered through a pad of Celite, washed with H2O (10 mL), andextracted with EtOAc (5 × 20 mL). The organic phase was separated,dried over Na2SO4, filtered, and concentrated in vacuo. The resultingresidue was purified by silica gel column chromatography to affordthe desired methylated product.

References:

Tang, Yu;Yu, Biao [Synthesis,2022,vol. 54,# 10,p. 2373 - 2390]