Dimethylformamide → 2-(3-iodophenyl)-N-(2-methoxyethyl)acetamide

To a solution of 3 iodophenylacetic acid (1.12 g, 4.3 mmol) in dichloromethane (50 mL) was added oxalyl chloride (0.75 mL, 8.6 mmol) and DMF (0.05 mL). The mixture was stirred for 1 h at room temperature and concentrated. The residue was dissolved in dry THF (40 mL) and 2-methoxyethylamine (2.0 mL, 23 mmol) was added. The mixture was stirred for 2 h and concentrated. The residue was partitioned between water and ethyl acetate, the organic phase was collected, washed with 1M HCl, water, saturated NaHCO3, brine, dried (MgSO4), filtered and concentrated to afford pure 151 (1.23 g, 89%). 1H NMR (400 MHz, CDCl3) δ (ppm): 7.64-7.61 (m, 2H), 7.26-7.24 (m, 1H), 7.10-7.06 (m, 1H), 5.81 (br s, 1H), 3.49 (s, 2H), 3.44-3.40 (m, 4H), 3.32 (s, 1H). MS (m/z): 320.1 (M+H).

1. concentrationconcentrated
2. dissolutionThe residue was dissolved in dry THF (40 mL)
3. stirringThe mixture was stirred for 2 h
4. concentrationconcentrated
5. customThe residue was partitioned between water and ethyl acetate
6. customthe organic phase was collected
7. washwashed with 1M HCl, water, saturated NaHCO3, brine
8. dry with materialdried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated

ORD record

ord-813b314ecec249949d1325c037b6533d

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08389541B2