Thionyl Chloride → HCID 68409591, compound

HRID 1511603Notes

Reaction equation

HRID 1511603 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:8][CH2:9][C:10]([OH:12])=O.S(Cl)(Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl.CN(C=O)C>[CH2:16]([O:15][C:13]([N:7]1[CH2:8][CH2:9][C:10](=[O:12])[C:3]2[CH:4]=[CH:5][O:1][C:2]=2[CH2:6]1)=[O:14])[CH3:17]

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 6451240Aluminum(III) ChlorideHCID 684123413-[(Furan-2-ylmethyl)(ethoxycarbonyl)amino]propanoic acid

Product 1

HCID 68409591HCID 68409591, compoundYield 41.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

3-[(Furan-2-ylmethyl)(ethoxycarbonyl)amino]propionic acid (3.6 g) prepared in the step 4 was dissolved in 300 mL of methylene chloride, then 2.66 g of thionyl chloride and 5 drops of DMF were added thereto and the mixture was heated to reflux for 3 hours. The reaction solution was cooled, 20.0 g of aluminum chloride was added thereto and the mixture was heated to reflux again for 30 minutes. The reaction solution was poured over 300 mL of ice water, the organic layer was separated, washed with water and a saturated solution of sodium chloride successively and dried over anhydrous magnesium sulfate and the solvent was evaporated in vacuo therefrom. The residue was purified by silica gel column chromatography to give 1.38 g of the objective compound as yellow liquid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 hours
  3. temperatureThe reaction solution was cooled
  4. temperaturethe mixture was heated
  5. temperatureto reflux again for 30 minutes
  6. customthe organic layer was separated
  7. washwashed with water
  8. dry with materiala saturated solution of sodium chloride successively and dried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated in vacuo
  10. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-58fedf88fb53449b84011c39cbb6ce9d
Source dataset
uspto-grants-2012_07
Patent number
US08217031B2

Reaction notes

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