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

HRID 745197Notes

Reaction equation

HRID 745197 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[CH2:13]([N:15]([CH2:19]C)[CH2:16][CH2:17][NH2:18])C.[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].[CH3:19][N:15]([CH3:13])[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]

Participants

6

Reactant 3

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

Product 1

HCID 86740886N'-[2-(Dimethylamino)ethyl]-N-(1-methylethyl)-N-[4-(phenylsulfonyl)butyl]urea hydrateYield 74.9%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 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. 1H NMR (CDCl3)δ7.8 (m, 5, aromatic), 5.25 (t, 1, NH), 4.15 (m, 1, methine), 3.2 (m, 6, SO2CH2 and methylenes adjacent to amide nitrogen, 2.5), (m, 6, ##STR28## 1.7 (m, 4, aliphatic--CH2CH2), 1.1 (m, 12, CH3).

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-894cde5f748548c09385d7af9b17257c
Source dataset
uspto-grants-1986_07
Patent number
US04597902

Reaction notes

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