Thionyl Chloride → Aniline, N-(2-chloroethyl)-N-methyl-

In a mixture of compound 2a (1.25 g, 8.3 mmol) and CH2Cl2 (50 mL), SOCl2 (1.2 mls, 16.5 mmol) was added dropwise over 20 min. During addition the solution turned from colorless to yellow. After the addition was complete, the mixture was heated to reflux for one hour. After cooling to room temperature, the mixture was quenched carefully with cold, saturated aqueous K2CO3 (50 mL). The mixture was then extracted with CH2Cl2, and the combined organic layer was washed with brine and dried over Na2SO4. The solvent was evaporated and the residue was purified by silica gel column chromatography with hexane/EtOAc to provide the compound 2b (0.55 g, 3.2 mmol, 39.3% yield) as a yellow oil. HRMS (ESI, positive) m/z calcd. for C9H13ClN [M+H]+: 170.07310, found: 170.07309. 1H NMR (400 MHz, Chloroform-d) δ 7.24 (dd, J=8.8, 7.3 Hz, 2H), 6.73 (m, J=14.2, 7.6 Hz, 3H), 3.71-3.56 (m, 4H), 3.00 (s, 3H).

1. additionwas added dropwise over 20 min
2. additionDuring addition the solution
3. additionAfter the addition
4. temperaturethe mixture was heated
5. temperatureto reflux for one hour
6. customthe mixture was quenched carefully with cold, saturated aqueous K2CO3 (50 mL)
7. extractionThe mixture was then extracted with CH2Cl2
8. washthe combined organic layer was washed with brine
9. dry with materialdried over Na2SO4
10. customThe solvent was evaporated
11. customthe residue was purified by silica gel column chromatography with hexane/EtOAc

ORD-Eintrag

ord-4f3d669819524c559d2d7032f6a1acdc

Quelldatensatz

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09394233B2