Hydrochloric Acid → Agn-194310

Temperature

40 °C

Two ml of a 2 M solution of NaOH were added to a solution of ethyl 4[[4-(4-ethylphenyl)-2,2-dimethyl-[2H]-thiochromen-6-yl]-ethynyl]benzoate in THF and ethanol. The solution was heated to 40° C., stirred overnight, then cooled to room temperature. The reaction mixture was acidified with 1 N HCl (4 ml). At the beginning of the process, the reaction mixture formed a heterogeneous system. The mixture was extracted with ethyl acetate (25 ml×2). The combined organic layers were washed with 10 ml water, saturated aqueous NaCl, and dried with NaSO4, and the solvent was removed under reduced pressure. The residual solid (0.31 gram) was recrystallized from acetonitrile (25 ml) to yield 4-[[4-(4-ethylphenyl)-2,2-dimethyl-(2H)-thiochroman-6-yl]-ethynyl]benzoic acid, (AGN194310) (0.236 gram, 70%) as a colorless solid (m.p. 210-212° C.) [1H-NMR (DMSO-d6): d8.2 (s, 2H), d7.8 (s, 2H), d7.6 (s, 2H), d7.4 (s, 2H), d7.2 (s, 2H), d7.0 (s, 1H), d6.0 (s, 1H), d2.6 (t, 2H, J=35 Hz), d1.6 (s, 6H), d1.4 (t, 3H, J=46 Hz)].

1. temperaturecooled to room temperature
2. customAt the beginning of the process, the reaction mixture formed a heterogeneous system
3. extractionThe mixture was extracted with ethyl acetate (25 ml×2)
4. washThe combined organic layers were washed with 10 ml water, saturated aqueous NaCl
5. dry with materialdried with NaSO4
6. customthe solvent was removed under reduced pressure
7. customThe residual solid (0.31 gram) was recrystallized from acetonitrile (25 ml)

ORD record

ord-b4d679c73b1d46e59035db9db3ae5583

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07955852B2