1,4-Dioxane → HCID 46199367, compound

HRID 717625Notes

Reaction equation

HRID 717625 reaction equation
[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:25])[NH:17][CH2:18][CH2:19][C:20]([O:22]CC)=[O:21])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].O1CCOCC1>>[CH2:1]([C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:16](=[O:25])[NH:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

3

Reactant 2

HCID 312751,4-DioxaneHCID 66615004Ethyl 3-(3-(4-octylphenyl)ureido)propanoate

Product 1

HCID 46199367HCID 46199367, compoundYield 65.5%

Procedure

To a solution of the product of Step A (0.05 g; 0.143 mmol) in dioxane (1 ml) 2N KOH (0.36 ml; 0.72 mmol) was added and the mixture was refluxed for 15 min, cooled to room temperature and evaporated to dryness under reduced pressure. The residue was diluted to 2 ml with H2O and filtered. The filtrate was acidified to pH ˜4 with citric acid. The solid formed was filtered off, washed with H2O (3×2 ml), dried in vacuo to give the title compound (0.03 g; 65%), as a colourless solid. 1H-NMR (CD3OD+CDCl3) 7.16 (d, 2H, J=8.4 Hz); 7.0 (d, 2H, J=8.4 Hz); 4.21 (s, CD3OH); 3.4 (t, 2H, J=6.7 Hz); 2.73 (m, 4H); 2.5-2.44 (m, 4H); 1.5 (m, 2H); 1.2 (m, 10H); 0.81 (m, 3H).

Workup

  1. temperaturethe mixture was refluxed for 15 min
  2. customevaporated to dryness under reduced pressure
  3. additionThe residue was diluted to 2 ml with H2O
  4. filtrationfiltered
  5. customThe solid formed
  6. filtrationwas filtered off
  7. washwashed with H2O (3×2 ml)
  8. customdried in vacuo

Sources & evidence

ORD record
ord-1956ca2cf9e64806bceeadd03ba1f5de
Source dataset
uspto-grants-2015_11
Patent number
US09193716B2

Reaction notes

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