Reaction #4324

Reaction equation

N,N-diethyl-N'-methylethylenediamine

triethylamine

citric acid

N-(1-methylethyl)-N-[2-(phenylsulfonyl)ethyl]carbamic chloride

→

N-[2-(Diethylamino)ethyl]-N-methyl-N'-(1-methylethyl)-N'-[2-(phenylsulfonyl)ethyl]urea citrate hydrate

Solvents

tetrahydrofuran

methanol

ether

Conditions

Workup

1. 1
   OtherThe solvent was removed in vacuo
2. 2
   workup.DISSOLUTIONthe residue was dissolved in a 60/40 mixture of ether and methylene chloride
3. 3
   ExtractionThis solution was extracted with several portions of water
4. 4
   Dryingwas dried over magnesium sulfate
5. 5
   OtherThe solvent was removed in vacuo
6. 6
   Otherto give an oil
7. 7
   OtherA solid precipitated
8. 8
   Otherto give 11.08 g (82.4%) of white, crystalline solid

Procedure

A mixture of 6.65 g (0.023 mole) of N-(1-methylethyl)-N-[2-(phenylsulfonyl)ethyl]carbamic chloride; 3.0 g (0.023 mole) of N,N-diethyl-N'-methylethylenediamine and triethylamine (2.7 g, 0.0267 mole) in 400 ml of tetrahydrofuran was stirred at room temperature for 10 hr. The solvent was removed in vacuo, and the residue was dissolved in a 60/40 mixture of ether and methylene chloride. This solution was extracted with several portions of water and was dried over magnesium sulfate. The solvent was removed in vacuo to give an oil. This was dissolved in methanol, an excess of citric acid was added, and ether was added. A solid precipitated to give 11.08 g (82.4%) of white, crystalline solid; m.p. 77°-82° C.

Source