Hydrochloric Acid → HCID 44185545, compound
Reaction equation
C([O:3][C:4](=[O:19])[C:5]1[CH:10]=[C:9]([CH:11]([S:13][CH3:14])[CH3:12])[CH:8]=[N:7][C:6]=1[C:15]([F:18])([F:17])[F:16])C.[OH-].[Li+].Cl>O1CCCC1>[CH3:14][S:13][CH:11]([C:9]1[CH:8]=[N:7][C:6]([C:15]([F:18])([F:17])[F:16])=[C:5]([CH:10]=1)[C:4]([OH:19])=[O:3])[CH3:12]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a dry 50 mL glass vial equipped with magnetic stirrer, and nitrogen inlet, was charged 0.5 g (0.00170 moles) of 5-(1-methylthioethyl)-2-trifluoromethylnicotinic acid ethyl ester, and 10 mL of tetrahydrofuran (THF). The solution was cooled to about 0° C. and 5.1 mL of 1N aqueous lithium hydroxide solution (0.00511 moles) was added slowly via syringe. The reaction was stirred at 0° C. for 1 hour, then overnight at ambient temperature. An aliquot was analyzed by thin layer chromatography (TLC) and high performance liquid chromatography (HPLC), which indicated that the reaction was essentially complete. The mixture was acidified to pH=2 with 1 M aqueous hydrochloric acid, and extracted with 3 aliquots of 50 mL of ethyl acetate. The extract was dried over anhydrous magnesium sulfate (MgSO4), filtered, and concentrated under vacuum on a rotary evaporator to afford 0.410 g of the title compound as a tan solid. 1H NMR (CDCl3): δ 1.66 (d, 3H), 1.96 (s, 3H), 3.98 (q, 1H), 8.01 (bs, 1H), 8.30 (s, 1H), and 8.80 (s, 1H).
Workup
- customovernight
- customat ambient temperature
- extractionextracted with 3 aliquots of 50 mL of ethyl acetate
- dry with materialThe extract was dried over anhydrous magnesium sulfate (MgSO4)
- filtrationfiltered
- concentrationconcentrated under vacuum on a rotary evaporator
Sources & evidence
- ORD record
- ord-a324e45536a14a5e9dd826669028b5b7
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08318946B2
Reaction notes
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