4-Octylaniline → Ethyl 3-(3-(4-octylphenyl)ureido)propanoate

HRID 2046041Notes

Reaction equation

HRID 2046041 reaction equation
[CH2:1]([C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[N:16]([CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:17]=[O:18]>C(Cl)Cl>[CH2:1]([C:9]1[CH:10]=[CH:11][C:12]([NH:13][C:17](=[O:18])[NH:16][CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:14][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 853464-OctylanilineHCID 2733373Ethyl 3-isocyanatopropanoate

Product 1

HCID 66615004Ethyl 3-(3-(4-octylphenyl)ureido)propanoateYield 87.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-n-octylaniline (0.1 g; 0.49 mmol) ethyl 3-isocyanatopropionate (0.08 g; 0.54 mmol) was added at room temperature. The resulting mixture was diluted to 1 ml with CH2Cl2, refluxed for 30 min and evaporated to dryness. The residue was treated with Et2O (5 ml) and the solid formed was filtered off and dried to give the title compound (0.15 g; 87%), as colourless crystals. 1H-NMR (CDCl3) 7.22-7.07 (m, 4H); 6.34 (broad s, 1H); 5.34 (m, 1H); 4.15-4.07 (m, 2H); 3.54-3.46 (m, 2H); 2.73 (m, 4H); 2.57-2.51 (m, 4H); 1.58 (m, 2H); 1.27-1.19 (m, 13H); 0.86 (m, 3H).

Workup

  1. temperaturerefluxed for 30 min
  2. customevaporated to dryness
  3. additionThe residue was treated with Et2O (5 ml)
  4. customthe solid formed
  5. filtrationwas filtered off
  6. customdried

Sources & evidence

ORD record
ord-a964d9a3307148689209a9805e3328d9
Source dataset
uspto-grants-2013_11
Patent number
US08592399B2

Reaction notes

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