Reaction #4378

Reaction equation

methylene chloride

oxalyl chloride

2-iodo-5-methoxybenzeneacetic acid

dimethylamine

→

N,N-dimethyl-2-iodo-5-methoxybenzeneacetamide

Solvents

toluene

DMF

Conditions

Workup

1. 1
   TemperatureThe solution was cooled to 0° C.
2. 2
   Temperatureto warm to room temperature
3. 3
   workup.STIRRINGstir for three hours
4. 4
   WashThe organic layer was washed with water, dilute hydrochloric acid, and sodium hydroxide
5. 5
   DryingThe organic layer was dried with MgSO4
6. 6
   Otherevaporated in vacuo

Procedure

A 16.7 g (0.19 mole) sample of oxalyl chloride was added dropwise at 0° C. to a solution of 50.0 g (0.17 mole) of 2-iodo-5-methoxybenzeneacetic acid in 310 ml dry toluene and 31.7 ml of DMF. The mixture was allowed to warm to room temperature and stir for 16 hours. The solution was cooled to 0° C. and dimethylamine gas was admitted until the mixture was strongly basic. The mixture was allowed to warm to room temperature and stir for three hours and methylene chloride was added. The organic layer was washed with water, dilute hydrochloric acid, and sodium hydroxide. The organic layer was dried with MgSO4 and evaporated in vacuo to give 54.2 g of N,N-dimethyl-2-iodo-5-methoxybenzeneacetamide, mp 86°-89° C.

Source