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

HRID 717624Notes

Reaction equation

HRID 717624 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-085ef5e6617d40ddbf04aaf8eca021f7
Source dataset
uspto-grants-2015_11
Patent number
US09193716B2

Reaction notes

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