Phosgene → HCID 19362170, compound

HRID 376511Notes

Reaction equation

HRID 376511 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10](OC)=[C:9]([O:15][CH3:16])[CH:8]=1.[C:18](=O)([O-])[O-:19].[Na+].[Na+].[C:24](Cl)(Cl)=[O:25].C(N(CC)CC)C>C1(C)C=CC=CC=1.O>[CH3:16][O:15][C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][C:10]=1[O:25][CH3:24])[CH2:6][N:5]1[CH:4]=[C:3]([O:2][CH3:1])[O:17][C:18]1=[O:19]

Participants

7

Reactant 4

HCID 6371Phosgene2×HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 19362173HCID 19362173, compound

Product 1

HCID 19362170HCID 19362170, compoundYield 43.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
15 °C

Procedure

In 30 ml of toluene was dissolved 4.78 g (20 mmol) of N-(3,4-dimethoxybenzyl)-glycine-methyl ester, and to the solution was added an aqueous solution containing 1.17 g (11 mmol) of anhydrous sodium carbonate dissolved in water. The mixture was cooled to 15° C. and 2.18 g (22 mmol) of a phosgene gas was blown under stirring to carry out the reaction. After completion of the phosgene blowing, the mixture was further stirred at room temperature for 2 hours. After completion of the reaction, the aqueous layer was separated from the resulting reaction mixture (1). The toluene layer was dried over anhydrous magnesium sulfate followed by filtration, and 2.02 g (20 mmol) of triethylamine was added to the filtrate and the mixture was reacted at 120° C. for 17 hours. After completion of the reaction, the resulting reaction mixture (2) was cooled to room temperature, and the precipitated triethylamine hydrochloride was removed by filtration. The filtrate was washed with 100 ml of water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting concentrated residue was applied to silica gel column chromatography (eluent; hexane:ethyl acetate=4:1 (volume ratio)) to obtain 1.74 g (4.8 mmol) of 3-(3,4-dimethoxybenzyl)-5-methoxy-2(3H)oxazolone as white crystals. (Yield based on N-(3,4-dimethoxybenzyl)-glycine-methyl ester 32.8%)

Workup

  1. additionto the solution was added an aqueous solution
  2. customthe reaction
  3. customAfter completion of the reaction
  4. customthe aqueous layer was separated from the resulting reaction mixture (1)
  5. dry with materialThe toluene layer was dried over anhydrous magnesium sulfate
  6. additionwas added to the filtrate
  7. customthe mixture was reacted at 120° C. for 17 hours
  8. customAfter completion of the reaction
  9. temperaturewas cooled to room temperature
  10. customthe precipitated triethylamine hydrochloride was removed by filtration
  11. washThe filtrate was washed with 100 ml of water
  12. dry with materialdried over anhydrous magnesium sulfate
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a215b8ba8c834117a78be2b5993cd039
Source dataset
uspto-grants-2000_02
Patent number
US06020496

Reaction notes

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