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

HRID 4221
Notes
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Reaction equation

HRID 4221 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[CH2:13]([N:15]([CH2:20][CH3:21])[CH2:16][CH:17]([NH2:19])[CH3:18])[CH3:14].[C:22]1([S:28]([CH2:31][CH2:32][NH:33][CH:34]([CH3:36])[CH3:35])(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O1CCCC1>[CH2:13]([N:15]([CH2:20][CH3:21])[CH2:16][CH:17]([NH:19][C:1](=[O:2])[N:33]([CH:34]([CH3:36])[CH3:35])[CH2:32][CH2:31][S:28]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)(=[O:29])=[O:30])[CH3:18])[CH3:14]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 13655034N-(2-phenylsulfonylethyl)-2-propanamineHCID 16643481(2-Aminopropyl)diethylamine

Product 1

HCID 20152789N'-[2-(Diethylamino)-1-methylethyl]-N-(1-methylethyl)-N-[2-(phenylsulfonyl)ethyl]ureaYield 59.5%

Reagents, catalysts & solvents 1

HCID 8028Tetrahydrofuran
Solvent
2×

Procedure

A mixture of 12.15 g (0.075 mole) of 1,1'-carbonyl diimidazole and 7.50 g (0.0476 mole) of 1-diethylamino-2-propanamine in 400 ml of tetrahydrofuran was stirred at room temperature for 1 hr. A solution of 12.26 g (0.054 mole) of N-[2-(phenylsulfonyl)ethyl]-2-propanamine in 50 ml of tetrahydrofuran was added, and the solution was refluxed for 19 hr. The solvent was removed in vacuo, and the residue was dissolved in a 50/50 mixture of methylene chloride and ether. The organic solution was extracted with several portions of water and was dried over magnesium sulfate. The solvent was removed in vacuo to give an oil. Flash chromatography on silica gel (elution with methanol) gave 10.87 g (52.3 g) of clear colorless oil.

Workup

  1. temperaturethe solution was refluxed for 19 hr
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in a 50/50 mixture of methylene chloride and ether
  4. extractionThe organic solution was extracted with several portions of water
  5. dry with materialwas dried over magnesium sulfate
  6. customThe solvent was removed in vacuo
  7. customto give an oil

Sources & evidence

ORD record
ord-676a05e13ec14819a379f9e941d94caf
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