Triethylamine → Methyl 2-[2-Hydroxy-3-[N-[2-[N-(phenylaminocarbonyl)amino]ethyl]amino]propoxy]benzoate

HRID 2308965Notes

Reaction equation

HRID 2308965 reaction equation
Cl.[C:2]1([NH:8][C:9]([NH:11][CH2:12][CH2:13][NH2:14])=[O:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[O:22]1[CH2:36][CH:23]1[CH2:24][O:25][C:26]1[CH:35]=[CH:34][CH:33]=[CH:32][C:27]=1[C:28]([O:30][CH3:31])=[O:29]>CO>[OH:22][CH:23]([CH2:36][NH:14][CH2:13][CH2:12][NH:11][C:9]([NH:8][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[CH2:24][O:25][C:26]1[CH:35]=[CH:34][CH:33]=[CH:32][C:27]=1[C:28]([O:30][CH3:31])=[O:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 279510Methyl 2-(oxiran-2-ylmethoxy)benzoateHCID 198637503-(2-Aminoethyl)-1-phenylurea hydrochloride

Product 1

HCID 13030944Methyl 2-[2-Hydroxy-3-[N-[2-[N-(phenylaminocarbonyl)amino]ethyl]amino]propoxy]benzoateYield 7.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

4.8 g of N-phenyl-N'-(2-aminoethyl)urea HCl salt (0.024 mole) was placed in 100 ml of methanol, and 2.5 g of triethylamine (0.024 mole) was added. While this reaction mixture was being stirred, a solution of 5 g of methyl 2-(2,3-epoxypropoxy)benzoate (0.024 mole) in 25 ml methanol was added slowly. The solution was then heated to reflux for 4 hours. The methanol was removed under reduced pressure and the resulting gel-like solid was dissolved in 100 ml of methylene chloride. The organic layer was washed twice with 100 ml of water and dried over anhydrous magnesium sulfate. Removal of the methylene chloride left an oil which was dissolved in 50 ml of methanol/ethyl ether (1:1) from which the product crystallized slowly upon refrigeration to afford 0.7 g (7.5%) of product having a melting point of 133°-134° C. The compound was identified by its NMR spectrum and elemental analysis.

Workup

  1. temperatureThe solution was then heated
  2. temperatureto reflux for 4 hours
  3. customThe methanol was removed under reduced pressure
  4. dissolutionthe resulting gel-like solid was dissolved in 100 ml of methylene chloride
  5. washThe organic layer was washed twice with 100 ml of water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customRemoval of the methylene chloride
  8. waitleft an oil which
  9. dissolutionwas dissolved in 50 ml of methanol/ethyl ether (1:1) from which the product
  10. customcrystallized slowly upon refrigeration

Sources & evidence

ORD record
ord-fcf68041adfc4728a2877f17f8d72e1b
Source dataset
uspto-grants-1987_09
Patent number
US04692446

Reaction notes

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