반응 #4312

반응 방정식

2-(phenylsulfonyl)ethanamine

1,1'-carbonyldiimidazole

citric acid

N,N,N'-triethylethylenediamine

→

white crystalline solid

수율 52.0%

N-[2-(Diethylamino)ethyl]-N-ethyl-N'-[2-(phenylsulfonyl)ethyl]urea citrate

수율 52.0%

용매

tetrahydrofuran

methanol

ether

tetrahydrofuran

반응 조건

후처리

1. 1
   온도the mixture was refluxed for 16 hr
2. 2
   기타The solvent was removed in vacuo
3. 3
   기타the residue was partitioned between a mixture of 300 ml of methylene chloride and 500 ml of ether and water
4. 4
   건조The organic phase was dried over magnesium sulfate
5. 5
   기타the solvent was removed in vacuo
6. 6
   기타to give an oil
7. 7
   workup.ADDITIONwas added
8. 8
   기타A white precipitate formed

실험 절차

A solution of 5.55 g (0.030 mole) of 2-(phenylsulfonyl)ethanamine and 5.35 g (0.033 mole) of 1,1'-carbonyldiimidazole in 400 ml of tetrahydrofuran was stirred at room temperature for 1 hr. A solution of 4.62 g (0.032 mole) of N,N,N'-triethylethylenediamine in 50 ml of tetrahydrofuran was added, and the mixture was refluxed for 16 hr. The solvent was removed in vacuo, and the residue was partitioned between a mixture of 300 ml of methylene chloride and 500 ml of ether and water. The organic phase was dried over magnesium sulfate, and the solvent was removed in vacuo to give an oil. A solution of the oil in methanol was treated with an equivalent of citric acid and ether was added. A white precipitate formed to give 8.54 g (52.0%) of white crystalline solid, m.p. 105°-107° C.

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