Methylamine → HCID 59570185, compound

Temperature

95 °C

1 drop of Et3N (catalytic) was added to a stirred solution of 3,5-bis(ethoxycarbonyl)benzoic acid (0.42 g, 1.5 mmol, 1 eq) in SOCl2 (4 mL, 6.54 g, 55 mmol, 37 eq) under Ar. The solution was heated to reflux at 95° C. After 2 h the reaction was cooled to room temperature, and the solvent was removed in vacuo. The resulting yellow oil was placed under Ar and dissolved in 5 mL anh. CH2Cl2. The solution was cooled to 0° C., and MeNH2 (2.0 M in THF, 2.7 mL, 5.4 mmol, 3.6 eq) was added with stirring. After stirring for 1 h, Et3N (0.2 mL, 0.15 g, 1.5 mmol, 1 eq) was added. The reaction was stirred at 0° C. to room temperature overnight. The solvent was removed in vacuo. The residue was diluted with saturated NaHCO3/water and extracted with EtOAc (×3). The combined organics were washed with water (×2), brine (×1), and dried over Na2SO4. The inorganics were filtered off, and the solvent was removed in vacuo yielding 0.2914 g (1.0 mmol, 70% yield) of diethyl 5-(methylcarbamoyl)isophthalate.

1. temperatureThe solution was heated
2. temperatureAfter 2 h the reaction was cooled to room temperature
3. customthe solvent was removed in vacuo
4. dissolutiondissolved in 5 mL anh. CH2Cl2
5. temperatureThe solution was cooled to 0° C.
6. stirringAfter stirring for 1 h
7. stirringThe reaction was stirred at 0° C. to room temperature overnight
8. customThe solvent was removed in vacuo
9. additionThe residue was diluted with saturated NaHCO3/water
10. extractionextracted with EtOAc (×3)
11. washThe combined organics were washed with water (×2), brine (×1)
12. dry with materialdried over Na2SO4
13. filtrationThe inorganics were filtered off
14. customthe solvent was removed in vacuo

ORD record

ord-75c005afd88d457e8fc4aab5d76d3955

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08299267B2