Dimethylamine → HCID 58994407, compound

Temperature

80 °C

A flask was charged with 4.60 g (19.9 mmol) of solid 2-(4-nitro-phenyl)-ethanesulfonic acid (as prepared in Example 26, step (b)), which was treated with 29.0 mL (398 mmol) of thionyl chloride and heated to 80° C. for 6 h. Solvents were evaporated in vacuo, and the resulting solid was dried overnight under high vacuum. A solution of 2.12 g (8.49 mmol) of this solid sulfonyl chloride in 40 mL CH2Cl2 was treated with 15.0 mL (127 mmol) of 40% w/v aqueous dimethylamine and stirred at RT for 16 h then warmed to 40° C. for 3 h. The mixture was diluted with CH2Cl2 (100 mL) and washed with water (2×50 mL). The aqueous layer was extracted with CH2Cl2 (50 mL). The combined organic layers were dried (MgSO4) and concentrated in vacuo. Silica gel chromatography of the residue on a 50-g Varian MegaBond Elut SPE column with 50% EtOAc-hexane afforded 912 mg (41%) of the title compound as an off-white solid: 1H-NMR (CD3OD; 400 MHz): δ 8.20 (d, 2H, J=8.8 Hz), 7.41 (d, 2H, J=8.8 Hz), 3.29-3.14 (m, 4H), 2.89 (s, 6H).

1. customSolvents were evaporated in vacuo
2. customthe resulting solid was dried overnight under high vacuum
3. temperaturethen warmed to 40° C. for 3 h
4. washwashed with water (2×50 mL)
5. extractionThe aqueous layer was extracted with CH2Cl2 (50 mL)
6. dry with materialThe combined organic layers were dried (MgSO4)
7. concentrationconcentrated in vacuo

ORD record

ord-509cd98ce1e34b72af39b9302db28fe9

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09221797B2