4-Methylbenzoyl Chloride → Dimethyl 5-[(4-methylbenzoyl)amino]isophthalate

HRID 480672

Reaktionsgleichung

Reaktionsgleichung von HRID 480672
[NH2:1][C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C(N(C(C)C)CC)(C)C.[C:25]1([CH3:34])[CH:30]=[CH:29][C:28]([C:31](Cl)=[O:32])=[CH:27][CH:26]=1>C(Cl)(Cl)Cl>[CH3:10][O:9][C:7]([C:6]1[CH:5]=[C:4]([CH:3]=[C:2]([NH:1][C:31]([C:28]2[CH:29]=[CH:30][C:25]([CH3:34])=[CH:26][CH:27]=2)=[O:32])[CH:11]=1)[C:12]([O:14][CH3:15])=[O:13])=[O:8]

Komponenten

5

Edukt 3

HCID 134054-Methylbenzoyl Chloride2×HCID 66831Dimethyl 5-aminoisophthalateHCID 81531Diisopropylethylamine2×

Produkt 1

HCID 721197Dimethyl 5-[(4-methylbenzoyl)amino]isophthalateAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel3×

Versuchsvorschrift

To 1.20 g (5.74 mmol) of methyl 5-amino-3-(methoxycarbonyl)benzoate, compound 87, suspended in 50 mL of chloroform and 1.05 mL (6.00 mmol) of diisopropylethylamine was added 836 μL (6.32 mmol) of p-toluoyl chloride in 10 mL of chloroform over 30 min. The reaction was allowed to stir at ambient temperature for 2 hr. Then, another 100 μL (0.60 mmol) of diisopropylethylamine and 100 μL (0.76 mmol) of p-toluoyl chloride in 2 mL of chloroform was added. After an addition 30 min, the volatiles were removed by rotary evaporation and the resulting residue was dissolved in ethyl acetate and extracted with 0.1 N aqueous NaOH followed by extraction with water. The organic layer was dried (MgSO4), filtered, and volatiles removed in vacuo. This provided 1.86 g (5.68 mmol) of the desired compound. The product was identified by 1H NMR and mass spectroscopy and purity was assessed by RP-HPLC.

Aufarbeitung

  1. additionAfter an addition 30 min
  2. customthe volatiles were removed by rotary evaporation
  3. dissolutionthe resulting residue was dissolved in ethyl acetate
  4. extractionextracted with 0.1 N aqueous NaOH
  5. extractionfollowed by extraction with water
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. customvolatiles removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4dc31118c93f4d6299c5f6ab2af4819d
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06653321B1

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