Reaction #51668

Reaction equation

hexane

2-chloro-6-methanesulfonylmethyl-phenylamine

p-toluenesulfonic acid hydrate

ethyl acetate

→

N-(2-Chloro-6-methanesulfonylmethyl-phenyl)-formimidic acid methyl ester

Solvents

trimethyl orthoformate

Conditions

Workup

1. 1
   Temperatureto reflux
2. 2
   Temperatureheated at this temperature for 3 h
3. 3
   TemperatureAt the end of 3 h, the reaction was cooled
4. 4
   Otherevaporated to dryness

Procedure

The 2-chloro-6-methanesulfonylmethyl-phenylamine (2.04 g, 0.019 mole) of Step 4 was suspended in 15 ml trimethyl orthoformate and p-toluenesulfonic acid hydrate (0.21 g) was added. The reaction mixture was brought to reflux and heated at this temperature for 3 h. The reaction was monitored by tlc (3:7 ethyl acetate:hexane, silica gel) which showed the appearance of a new slightly less polar spot. At the end of 3 h, the reaction was cooled and evaporated to dryness to afford N-(2-Chloro-6-methanesulfonylmethyl-phenyl)-formimidic acid methyl ester.

Source