Dimethyl Sulfate → 2-[1-(Methanesulfonyl)ethyl]-6-(trifluoromethyl)aniline

A mixture of 50% NaOH (50 mL), CH2Cl2 (50 mL), triethylbenzylammonium chloride (30 mg), Me2SO4 (2.50 mL, 26.41 mmol) and 2-methylsulfonylmethyl-6-trifluoromethyl nitrobenzene 3 (6.8 g, 24.01 mmol) was stirred rapidly for 30 min. The mixture was poured onto ice/water (400 mL) and the organic layer separated. The solvent was removed and excess Me2SO4 removed at 60° C. and 0.7 mm, to give a yellow solid which was identified as the same product as in Example 2, i.e., 2-(1-methylsulfonylethyl)-6-trifluoromethyl nitrobenzene. The solid was transferred to a Parr bomb with EtOAc/EtOH (2:1, 100 mL, not all soluble). Five drops of acetic acid and Pd/carbon was added. The mixture was hydrogenated at 60° C. and 60 psi H2 for 15 hrs. The mixture was filtered and the solvent removed to give a brown solid. Washing with ether gave 4.03 g (15.07 mmol, 62.8%) of 2-(1-methylsulfonylethyl)-6-trifluoromethyl aniline as a white solid, mp 153°-5° C.

1. additionThe mixture was poured onto ice/water (400 mL)
2. customthe organic layer separated
3. customThe solvent was removed
4. customexcess Me2SO4 removed at 60° C.
5. custom0.7 mm, to give a yellow solid which
6. customwas hydrogenated at 60° C.
7. wait60 psi H2 for 15 hrs
8. filtrationThe mixture was filtered
9. customthe solvent removed
10. customto give a brown solid
11. washWashing with ether

ORD-Eintrag

ord-fa4b1b4b9c894fba9be2a69b46fe0c8d

Quelldatensatz

uspto-grants-1984_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04440964