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

HRID 4227
Notes
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Reaction equation

HRID 4227 reaction equation
[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][NH2:6])[CH3:2].[C:9](N1C=CN=C1)(N1C=CN=C1)=[O:10].[CH3:21][CH:22]([NH:24][CH:25]([CH3:36])[CH2:26][S:27]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)(=[O:29])=[O:28])[CH3:23]>O1CCCC1>[OH2:10].[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][NH:6][C:9](=[O:10])[N:24]([CH:22]([CH3:21])[CH3:23])[CH:25]([CH3:36])[CH2:26][S:27]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)(=[O:28])=[O:29])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 60993N,N-DiethylethylenediamineHCID 682631,1'-CarbonyldiimidazoleHCID 13655091N-(2-propyl)-1-(phenylsulfonyl)-2-propanamine

Product 1

HCID 13655155N'-[2-(Diethylamino)ethyl]-N-(1-methylethyl)-N-[1-methyl-2-(phenylsulfonyl)ethyl]urea hydrate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3.71 g (0.032 mole) of N,N-diethylethylenediamine and 5.83 (0.036 mole) of 1,1'-carbonyldiimidazole in 400 ml of tetrahydrofuran was stirred at room temperature for 1 hr. A solution of 8.30 g (0.030 mole) of N-(2-propyl)-1-(phenylsulfonyl)-2-propanamine in 50 ml of tetrahydrofuran was added and the solution was refluxed overnight. The solvent was removed in vacuo, and the residue was partitioned between ether and water. The ether solution was dried over magnesium sulfate and the solvent was removed in vacuo to give an oil. The oil was flash chromatographed (silica gel; elution with methanol) to give an oil. Crystallization from ether gave 0.54 g (4.5%) of white, crystalline solid, m.p. 75°-80° C.

Workup

  1. temperaturethe solution was refluxed overnight
  2. customThe solvent was removed in vacuo
  3. customthe residue was partitioned between ether and water
  4. dry with materialThe ether solution was dried over magnesium sulfate
  5. customthe solvent was removed in vacuo
  6. customto give an oil
  7. customchromatographed
  8. wash(silica gel; elution with methanol)
  9. customto give an oil
  10. customCrystallization from ether
  11. customgave 0.54 g (4.5%) of white, crystalline solid, m.p. 75°-80° C.

Sources & evidence

ORD record
ord-696537874e0c4dd5a445f74308693ec2
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