HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

N,N-Diethylethylenediamine → N'-[2-(Diethylamino)ethyl]-N-(1-methylethyl)-N-[4-(phenylsulfonyl)butyl]urea hydrate

HRID 4229
Notes
Print preview

Reaction equation

HRID 4229 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].[CH3:21][CH:22]([NH:24][CH2:25][CH2:26][CH2:27][CH2:28][S:29]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)(=[O:31])=[O:30])[CH3:23]>O1CCCC1.C(Cl)(Cl)Cl>[OH2:2].[CH2:13]([N:15]([CH2:19][CH3:20])[CH2:16][CH2:17][NH:18][C:1](=[O:2])[N:24]([CH:22]([CH3:21])[CH3:23])[CH2:25][CH2:26][CH2:27][CH2:28][S:29]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)(=[O:30])=[O:31])[CH3:14]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 60993N,N-DiethylethylenediamineHCID 682631,1'-CarbonyldiimidazoleHCID 13655072N-(1-methylethyl)-4-(phenylsulfonyl]-1-butylamine

Product 1

HCID 20152850N'-[2-(Diethylamino)ethyl]-N-(1-methylethyl)-N-[4-(phenylsulfonyl)butyl]urea hydrateYield 69.8%

Reagents, catalysts & solvents 2

HCID 6212Chloroform
Solvent
HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1,1'-carbonyldiimidazole (6.00 g, 0.037 mole) and N,N-diethylethylenediamine (4.00 g, 0.034 mole) was stirred at room temperature for 2 hours in 200 ml of tetrahydrofuran. A solution of N-(1-methylethyl)-4-(phenylsulfonyl]-1-butylamine (free base 7.99 g, 0.0313 mole) in 100 ml of tetrahydrofuran was added and the solution was heated overnight at reflux. The reaction was stripped to dryness and the residue dissolved in chloroform. The chloroform was extracted with water, dried (sodium sulfate), filtered, and removed in vacuo. A dark brown oil was obtained upon removal of chloroform. This oil was subjected to flash chromatography on Silica Gel using 0.1N ammonium hydroxide-methanol for elution. This chromatography furnished 5.37 g (42.2% yield) of clear oil after drying in vacuo 18 hours at 60° C.

Workup

  1. temperaturethe solution was heated overnight
  2. temperatureat reflux
  3. extractionThe chloroform was extracted with water
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. customremoved in vacuo
  7. customA dark brown oil was obtained upon removal of chloroform
  8. washThis oil was subjected to flash chromatography on Silica Gel using 0.1N ammonium hydroxide-methanol for elution

Sources & evidence

ORD record
ord-f4da05c15f66425caadd5d8639eb6bb2
Source dataset
uspto-grants-1988_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04724235

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes