Dibutylamine → Urea, N'-(4-acetylphenyl)-N,N-dibutyl-

HRID 582805Notes

Reaction equation

HRID 582805 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:19])OC2C=CC=CC=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH2:20]([NH:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH3:23].CCOC(C)=O>CS(C)=O>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11](=[O:19])[N:24]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:20][CH2:21][CH2:22][CH3:23])=[CH:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8148DibutylamineHCID 8857Ethyl AcetateHCID 80600999134-77-7

Product 1

HCID 10968248Urea, N'-(4-acetylphenyl)-N,N-dibutyl-Yield 96.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In a dry 100 mL flask equipped with an N2 inlet adapter, a rubber septum and a magnetic stirring bar, was placed phenyl N-(4-acetylphenyl)carbamate (6.38 g, 25 mmol) in DMSO (50 mL). Dibutylamine (4.42 mL, 26.25 mmol) was slowly added to the mixture. The resulting solution was stirred at room temperature for 15 min, after which time EtOAc (250 mL) was added to the reaction mixture. The latter was washed successively with H2O (2×50 mL), aqueous 1N HCl (100 mL), H2O (100 mL), aqueous 1N NaOH (100 mL) and brine (100 mL), dried (MgSO4) and concentrated under reduced pressure to give a crude solid. The solid was triturated with Et2O/hexane to yield 6.98 g (96% yield) of the title compound as a white solid.

Workup

  1. customIn a dry 100 mL flask equipped with an N2 inlet adapter
  2. washThe latter was washed successively with H2O (2×50 mL), aqueous 1N HCl (100 mL), H2O (100 mL), aqueous 1N NaOH (100 mL) and brine (100 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customto give a crude solid
  6. customThe solid was triturated with Et2O/hexane

Sources & evidence

ORD record
ord-4ea55f42a07947f08930a01ae63519a7
Source dataset
uspto-grants-1999_07
Patent number
US05925762

Reaction notes

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