Triethylamine → 3-(Ethoxycarbonylpropyl]urea

HRID 974013Notes

Reaction equation

HRID 974013 reaction equation
C([N:11]=[C:12]=[O:13])CCCCCCCCC.Cl.C(O[NH:23][CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])C1C=CC=CC=1.C(N(CC)CC)C>C1(C)C=CC=CC=1.CN(C=O)C>[CH2:30]([O:29][C:27]([CH2:26][CH2:25][CH2:24][NH:23][C:12](=[O:13])[NH2:11])=[O:28])[CH3:31]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 4420451Decyl isocyanateHCID 19987251Ethyl 4-(benzyloxyamino)butyrate hydrochloride

Product 1

HCID 543213273-(Ethoxycarbonylpropyl]ureaYield 180.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

Using the method of Example 2 above, but using ethyl 4-bromobutyrate, t-butyl N-[3-(ethoxycarbonyl)propyl]-N-benzyloxy carbamate was obtained as a colorless oil. This carbamate (6.17 g, 18.8 mmol) was dissolved in 3.3M HCl in ethyl acetate (50 ml) at room temperature under nitrogen. After one hour, the turbid solution was evaporated, and the residue was triturated with hexane. Filtration gave ethyl 4-(benzyloxyamino)butyrate hydrochloride as a white solid (4.59 g, 93% yield). To a solution of decyl isocyanate (0.92 g) in toluene (50 ml) was added this hydrochloride (1.40 g) in DMF (5 ml). Triethylamine (0.75 ml) was added, and the solution was stirred for one hour. The mixture was washed with 10% aqueous citric acid, and the organic solution was dried (MgSO4), filtered and evaporated. Purification by chromatography on silica gave N'-decyl-N-benzyloxy-N-[3-(ethoxycarbonylpropyl]urea as a colorless oil (1.58 g, 58% yield).

Workup

  1. washThe mixture was washed with 10% aqueous citric acid
  2. dry with materialthe organic solution was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customPurification by chromatography on silica

Sources & evidence

ORD record
ord-3e65a6c9213a4d2bab96e07fbf3570e3
Source dataset
uspto-grants-1991_11
Patent number
US05066658

Reaction notes

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