Methanol → Methyl 2-amino-4-iodobenzoate

Temperatur

65 °C

To 2-acetylamino-4-iodo-benzoic acid (13.8 g, 45.3 mmol) in 200 mL of dry methanol was added SOCl2 (32.7 mL, 453 mmol) dropwise at 0° C. The reaction mixture was then heated at 65° C. for 2 h. The reaction was then cooled to 0° C., an additional portion of SOCl2 (10 mL, 137 mmol) was added, and the reaction was heated at 65° C. for 2 h. The reaction was then cooled to 0° C., a final portion of SOCl2 (10 mL, 137 mmol) was added, and the reaction was heated at 65° C. for 48 h. The reaction was then cooled to 22° C. and concentrated in vacuo. The resulting residue was diluted with H2O and extracted with 3×150 mL CH2Cl2. The combined organic fractions were washed with brine and dried over Na2SO4 to give i-b (11.7 g, 93%): MS m/z=278 (M+H).

1. temperatureThe reaction was then cooled to 0° C.
2. temperaturethe reaction was heated at 65° C. for 2 h
3. temperatureThe reaction was then cooled to 0° C.
4. temperaturethe reaction was heated at 65° C. for 48 h
5. temperatureThe reaction was then cooled to 22° C.
6. concentrationconcentrated in vacuo
7. additionThe resulting residue was diluted with H2O
8. extractionextracted with 3×150 mL CH2Cl2
9. washThe combined organic fractions were washed with brine
10. dry with materialdried over Na2SO4
11. customto give i-b (11.7 g, 93%)

ORD-Eintrag

ord-098383dbc3e0469b827b4e8ee428e1ec

Quelldatensatz

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07935694B2