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

HRID 4216

Reaction equation

HRID 4216 reaction equation
[C:1]1([S:7]([CH2:10][CH2:11][NH2:12])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13](N1C=CN=C1)(N1C=CN=C1)=[O:14].[CH2:25]([N:27]([CH2:33][CH3:34])[CH2:28][CH2:29][NH:30][CH2:31][CH3:32])[CH3:26].[C:35]([OH:47])(=[O:46])[CH2:36][C:37]([CH2:42][C:43]([OH:45])=[O:44])([C:39]([OH:41])=[O:40])[OH:38]>O1CCCC1.CO.CCOCC>[C:35]([OH:47])(=[O:46])[CH2:36][C:37]([CH2:42][C:43]([OH:45])=[O:44])([C:39]([OH:41])=[O:40])[OH:38].[CH2:25]([N:27]([CH2:33][CH3:34])[CH2:28][CH2:29][N:30]([CH2:31][CH3:32])[C:13]([NH:12][CH2:11][CH2:10][S:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)(=[O:8])=[O:9])=[O:14])[CH3:26]

Participants

8

Reactant 4

HCID 311Citric AcidHCID 66040TriethylethylenediamineHCID 682631,1'-CarbonyldiimidazoleHCID 35454972-(Benzenesulfonyl)ethan-1-amine

Product 1

HCID 13655129N-[2-(Diethylamino)ethyl]-N-ethyl-N'-[2-(phenylsulfonyl)ethyl]urea citrateYield 52%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  1. temperaturethe mixture was refluxed for 16 hr
  2. customThe solvent was removed in vacuo
  3. customthe residue was partitioned between a mixture of 300 ml of methylene chloride and 500 ml of ether and water
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. customthe solvent was removed in vacuo
  6. customto give an oil
  7. additionwas added
  8. customA white precipitate formed

Sources & evidence

ORD record
ord-fefe59a7cdf245f1bf02e5ac9fe770f6
Source dataset
uspto-grants-1988_02
Patent number
US04724235

Linked notes

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