Reaction #56118

Reaction equation

thionyl chloride

1-(2',6'-dichlorophenyl)-2-(2',3'-bismethoxycarbonylguanidino) ethanol

sodium hydroxide

methyl alcohol

→

4,5-Dihydro-2-methoxycarbonylamino-5-(2',6'-dichlorophenyl)imidazole

Solvents

methylene chloride

water

Conditions

Workup

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   workup.ADDITIONAt the conclusion of the addition period
3. 3
   Temperaturethe resulting mixture refluxed for 60 minutes
4. 4
   OtherThe reaction solution was evaporated to low volume under vacuum and 50 ml of water
5. 5
   workup.ADDITIONadded
6. 6
   OtherThe precipitated solid was collected
7. 7
   Washwashed with methanol
8. 8
   Otherdried

Procedure

To 1 gram of 1-(2',6'-dichlorophenyl)-2-(2',3'-bismethoxycarbonylguanidino) ethanol dissolved in 20 ml of methylene chloride was added dropwise with cooling at 0° C. 0.35 g of thionyl chloride. At the conclusion of the addition period, the solution was stirred for an additional 60 minutes at room temperature. After the addition of 20 ml of methyl alcohol, a solution of 0.5 g of sodium hydroxide in 2 ml of water was added and the resulting mixture refluxed for 60 minutes. The reaction solution was evaporated to low volume under vacuum and 50 ml of water added. The precipitated solid was collected, washed with methanol, followed by water and dried. 4,5-Dihydro-2-methoxycarbonylamino-5-(2',6'-dichlorophenyl)imidazole was isolated, 0.3 g, m.p. 229-230 (dec.).

Source