Ethanol → Ethyl 4-(trifluoromethyl)thiazole-2-carboxylate
Reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[N:4]=[C:5]([C:8]([OH:10])=[O:9])[S:6][CH:7]=1.O=S(Cl)Cl.[CH3:17][CH2:18]O>>[CH2:17]([O:9][C:8]([C:5]1[S:6][CH:7]=[C:3]([C:2]([F:1])([F:11])[F:12])[N:4]=1)=[O:10])[CH3:18]Participants
4
Conditions
- Temperature
- 40 °C
Procedure
To a stirred solution of 4-trifluoromethylthiazole-2-carboxylic acid (98 g, 1 eq.) in EtOH (600 mL) was added dropwise SOCl2 (36 mL, 1 eq.). The mixture was stirred at 40° C. for 8 hrs and then at room temperature for 16 hrs. The reaction mixture was concentrated under reduced pressure and the residue was redissolved in DCM. Organics were washed with saturated aqueous NaHCO3 solution, dried over Na2SO4, filtered, and concentrated under reduced pressure to yield compound 281 as a brown solid in 96% yield. 1H NMR (CDCl3, 400 MHz) δ 1.45 (t, J=7.14 Hz, 3H), 4.49-4.54 (q, J=7.10 Hz, 2H), 8.02 (s, 1H).
Workup
- waitat room temperature for 16 hrs
- concentrationThe reaction mixture was concentrated under reduced pressure
- dissolutionthe residue was redissolved in DCM
- washOrganics were washed with saturated aqueous NaHCO3 solution
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-caba1721a4354acf81b6beb1c323457b
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08993595B2
Reaction notes
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