Hydrochloric Acid → HCID 18930641, compound

HRID 1598913Notes

Reaction equation

HRID 1598913 reaction equation
C[O:2][C:3]([CH2:5][NH:6][C:7](=[O:21])[NH:8][C:9]1[CH:10]=[C:11]([CH:18]=[CH:19][CH:20]=1)[C:12]([O:14][CH2:15][CH:16]=[CH2:17])=[O:13])=[O:4].Cl.O.C(=O)(O)[O-].[Na+]>C1COCC1>[CH2:15]([O:14][C:12]([C:11]1[CH:10]=[C:9]([NH:8][C:7](=[O:21])[NH:6][CH2:5][C:3]([OH:4])=[O:2])[CH:20]=[CH:19][CH:18]=1)=[O:13])[CH:16]=[CH2:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 18930538HCID 18930538, compound

Product 1

HCID 18930641HCID 18930641, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of allyl 3-(methoxycarbonylmethylureido)benzoate (5.27 g, 18.7 mmol) in THF (27 ml) is added 2N hydrochloric acid (37.4 ml), and the mixture is refluxed with stirring for 2.5 hours. After allowing to cool, water and an aqueous saturated sodium bicarbonate solution are added to the reaction solution to adjust the pH of the aqueous layer to 8, which is then extracted with ethyl acetate. Concentrated hydrochloric acid is added to the aqueous layer to adjust the pH to 1, followed by extraction with ethyl acetate. The organic layer is washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue is crystallized from toluene to obtain the objective compound (3.66 g). Yield 70%.

Workup

  1. temperaturethe mixture is refluxed
  2. temperatureto cool
  3. extractionis then extracted with ethyl acetate
  4. additionConcentrated hydrochloric acid is added to the aqueous layer
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer is washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue is crystallized from toluene

Sources & evidence

ORD record
ord-3fc809c78a3243ab9db31d0d9728d284
Source dataset
uspto-grants-1998_04
Patent number
US05739162

Reaction notes

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