Triethylamine → 298221-40-6

HRID 992846Notes

Reaction equation

HRID 992846 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:14])=[C:6]2[NH:12][C:11](=O)[O:10][C:8](=[O:9])[C:7]=12.C(N(CC)CC)C>CO>[NH2:12][C:6]1[C:5]([CH3:14])=[CH:4][CH:3]=[C:2]([Cl:1])[C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 22890221HCID 22890221, compound

Product 1

HCID 23446878298221-40-6

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

At 22° C., 110 g (0.52 mol of 6-chloro-3-methylisatoic anhydride were introduced into a mixture of 750 ml of methanol and 47.6 g (0.47 mol) of triethylamine, and the mixture was then stirred at 65° C. for 2 h. The reaction mixture was concentrated under reduced pressure and the residue was taken up in methylene chloride and extracted 3 times with 0.5 N aqueous sodium hydroxide solution. The mixture was dried over magnesium sulfate, filtered through silica gel and concentrated under reduced pressure, giving 45.5 g (43.8% of theory) of the title compound as a colorless oil with nD23=1.5765.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionextracted 3 times with 0.5 N aqueous sodium hydroxide solution
  3. dry with materialThe mixture was dried over magnesium sulfate
  4. filtrationfiltered through silica gel
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-da7b1bdb405e49098cc78eceaa7e2eae
Source dataset
uspto-grants-2002_10
Patent number
US06472349B1

Reaction notes

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