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N,N-Diethylethylenediamine → N'-[2-(Diethylamino)ethyl]-N-(1-methylethyl)-N-[2-(phenylsulfinyl)ethyl]urea

HRID 4223
Notes
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Reaction equation

HRID 4223 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[CH2:13]([N:15]([CH2:19][CH3:20])[CH2:16][CH2:17][NH2:18])[CH3:14].[C:21]1([S:27]([CH2:29][CH2:30][NH:31][CH:32]([CH3:34])[CH3:33])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O1CCCC1>[CH2:13]([N:15]([CH2:19][CH3:20])[CH2:16][CH2:17][NH:18][C:1](=[O:2])[N:31]([CH:32]([CH3:34])[CH3:33])[CH2:30][CH2:29][S:27]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:28])[CH3:14]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 60993N,N-DiethylethylenediamineHCID 682631,1'-CarbonyldiimidazoleHCID 13655080N-[2-(phenylsulfinyl)ethyl]-2-propanamine

Product 1

HCID 20152795N'-[2-(Diethylamino)ethyl]-N-(1-methylethyl)-N-[2-(phenylsulfinyl)ethyl]ureaYield 55.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent
2×

Procedure

A mixture of 4.70 g (0.029 mole) of 1,1'-carbonyldiimidazole- and 3.07 g (0.0265 mole) of N,N-diethylethylenediamine in 400 ml of tetrahydrofuran was stirred at room temperature for 1 hr. A solution of 8.00 g (0.0245 mole) of N-[2-(phenylsulfinyl)ethyl]-2-propanamine 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 dissolved in ether. The ether solution was extracted with several portions of water. The aqueous extract was extracted with ether and then with methylene chloride; these organic extracts were combined with the original ether solution. The organic solution was dried over magnesium sulfate, and the solvent was removed in vacuo to give an oil. Flash chromatography on silica gel (methanol) gave 4.84 g (55.9%) of oil:

Workup

  1. temperaturethe mixture was refluxed for 16 hr
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in ether
  4. extractionThe ether solution was extracted with several portions of water
  5. extractionThe aqueous extract
  6. extractionwas extracted with ether
  7. dry with materialThe organic solution was dried over magnesium sulfate
  8. customthe solvent was removed in vacuo
  9. customto give an oil

Sources & evidence

ORD record
ord-9fc3086f133b4cb882634b634e570ee1
Source dataset
uspto-grants-1988_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04724235

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes