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1,1'-Carbonyldiimidazole → N-(1-Methylethyl)-N'-[2-[methyl-(2-phenylethyl)amino]ethyl]-N-[2-(phenylsulfonyl)ethyl]urea hemihydrate

HRID 745182
Notes
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Reaction equation

HRID 745182 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=[O:2].[CH3:13][N:14]([CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:15][CH2:16][NH2:17].[CH3:26][CH:27]([NH:29][CH2:30][CH2:31][S:32]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)(=[O:34])=[O:33])[CH3:28].C[C:42](C)=[O:43].[C:45](OCC)(=[O:47])C>O1CCCC1.C(Cl)(Cl)Cl.C(OCC)C>[OH2:2].[CH3:28][CH:27]([N:29]([CH2:30][CH2:31][S:32]([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)(=[O:33])=[O:34])[C:42]([NH:17][CH2:16][CH2:15][N:14]([CH3:13])[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:43])[CH3:26].[CH3:28][CH:27]([N:29]([CH2:30][CH2:31][S:32]([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)(=[O:33])=[O:34])[C:45]([NH:17][CH2:16][CH2:15][N:14]([CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:13])=[O:47])[CH3:26]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 12488261N-Methyl-N-(2-phenylethyl)ethane-1,2-diamineHCID 13655034N-(2-phenylsulfonylethyl)-2-propanamineHCID 21584569Ethylacetate acetone

Product 1

HCID 70419535N-(1-Methylethyl)-N'-[2-[methyl-(2-phenylethyl)amino]ethyl]-N-[2-(phenylsulfonyl)ethyl]urea hemihydrate

Reagents, catalysts & solvents

2
HCID 8028TetrahydrofuranSolventHCID 21911965Chloroform etherSolvent

Procedure

A solution of 1,1'-carbonyldiimidazole (8.12 g, 0.05 mole) and N-methyl-N-(2-phenylethyl)-1,2-ethanediamine, 8.0 g (0.0045 mole) in 300 ml of tetrahydrofuran was stirred for 2 hours at room temperature. To the mixture was added 9.37 g (0.0412 mole) of 1-methyl-N-[2-(phenylsulfonyl)ethyl]ethanamine and the reaction was heated at gentle reflux overnight. The reaction was stripped to dryness and dissolved in chloroform-diethyl ether (50-50 v/v) and extracted with water. The organic phase was extracted with 1N sulfuric acid. (Approximately half the product was extracted with acid and half remained in the organic layer). The organic layer was extracted with dilute sodium hydroxide, dried, filtered, and the solvent removed to give an oil. The oil was subjected to column chromatography on Silica Gel using acetone-ethyl acetate as a eluant. This furnished 0.5 g (2.8%) of oil.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat gentle reflux overnight
  3. extractionextracted with water
  4. extractionThe organic phase was extracted with 1N sulfuric acid
  5. extraction(Approximately half the product was extracted with acid and half
  6. extractionThe organic layer was extracted with dilute sodium hydroxide
  7. customdried
  8. filtrationfiltered
  9. customthe solvent removed
  10. customto give an oil

Sources & evidence

ORD record
ord-0ae0a9dc6c934b61a16309de49d0b18f
Source dataset
uspto-grants-1986_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04597902

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes