Methanol → N'-[2-(Diethylamino)ethyl]-N-(1-methylethyl)-N-[5-(phenylsulfonyl)pentyl]urea hydrate

HRID 4230

Reaction equation

HRID 4230 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=[O:2].[CH2:13]([N:15]([CH2:19][CH3:20])[CH2:16][CH2:17][NH2:18])[CH3:14].[CH3:21][CH:22]([NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][S:30]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)(=[O:32])=[O:31])[CH3:23].[CH3:39][OH:40]>O1CCCC1.C(Cl)(Cl)Cl>[OH2:2].[CH2:13]([N:15]([CH2:19][CH3:20])[CH2:16][CH2:17][NH:18][C:39](=[O:40])[N:24]([CH:22]([CH3:23])[CH3:21])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][S:30]([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)(=[O:32])=[O:31])[CH3:14]

Participants

7

Reactant 4

HCID 887MethanolHCID 60993N,N-DiethylethylenediamineHCID 682631,1'-CarbonyldiimidazoleHCID 13655070N-(1-methylethyl)-5-(phenylsulfonyl)-1-pentanamine

Product 1

HCID 20152837N'-[2-(Diethylamino)ethyl]-N-(1-methylethyl)-N-[5-(phenylsulfonyl)pentyl]urea hydrateYield 66.6%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1,1'-carbonyldiimidazole (4.54 g, 0.028 mole) and N,N-diethylethylenediamine (2.90 g, 0.025 mole) in tetrahydrofuran was stirred for 1 hr at room temperature. A solution of N-(1-methylethyl)-5-(phenylsulfonyl)-1-pentanamine (6.74 g, 0.025 mole) in tetrahydrofuran (dried over 4 A molecular sieves) was added and the resulting solution was heated over night at gentle reflux. The reaction mixture was stripped to dryness and the residue dissolved in chloroform. The chloroform layer was extracted with water, dried (anhydrous sodium sulfate), filtered and the solvent removed to give a brown oil. The brown oil was subjected to flash column chromatography on Silica Gel using methanol for elution. Fractions of similar purity were combined, solvent removed, and the oil dried in vacuo at 60° C. overnight. This produced 7.00 g (66.6% yield) of brown oil.

Workup

  1. additionwas added
  2. temperaturethe resulting solution was heated over night at gentle reflux
  3. extractionThe chloroform layer was extracted with water
  4. dry with materialdried (anhydrous sodium sulfate)
  5. filtrationfiltered
  6. customthe solvent removed
  7. customto give a brown oil
  8. washfor elution
  9. customsolvent removed
  10. customthe oil dried in vacuo at 60° C. overnight

Sources & evidence

ORD record
ord-3bf903c0996240489547e5913b65a55e
Source dataset
uspto-grants-1988_02
Patent number
US04724235

Linked notes

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