Sodium Hydroxide → HCID 10244794, compound

HRID 722335Notes

Reaction equation

HRID 722335 reaction equation
[Cl:1][C:2]1[C:3]([CH3:21])=[CH:4][C:5]2[S:10][CH:9]([C:11]([F:14])([F:13])[F:12])[C:8]([C:15]([O:17]CC)=[O:16])=[CH:7][C:6]=2[CH:20]=1.[OH-].[Na+]>C1COCC1.C(O)C>[Cl:1][C:2]1[C:3]([CH3:21])=[CH:4][C:5]2[S:10][CH:9]([C:11]([F:13])([F:12])[F:14])[C:8]([C:15]([OH:17])=[O:16])=[CH:7][C:6]=2[CH:20]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 21883593HCID 21883593, compound

Product 1

HCID 10244794HCID 10244794, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The ester from Step 3 (2.02 g, 6.0 mmol) was dissolved in THF (10 mL) and ethanol (10 mL), treated with 2.5 N sodium hydroxide (5.5 mL, 13.8 mmol), and stirred at room temperature for 4.8 hours. The reaction mixture was concentrated in vacuo, acidified with 3 N HCl yielding a suspension. The solid was collected by filtration and was recrystallized from ethanol-water to yield the title compound as a yellow solid (0.20 g, 11%): mp 240.5–241.7° C. 1H NMR (acetone-d6/300 MHz) 7.99 (s, 1H), 7.67 (s, 1H), 7.43 (s, 1H), 4.99 (q, 1H, J=8.5 Hz), 2.39 (s, 3H). FABLRMS m/z 307 (M−H). FABHRMS m/z 306.9831 (M−H, Calc'd 306.9807). Anal. Calc'd for C12H8ClF3O2S: C, 46.69; H, 2.61; Cl, 11.48. Found: C, 46.78; H, 2.61; Cl, 11.41.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. filtrationThe solid was collected by filtration
  3. customwas recrystallized from ethanol-water

Sources & evidence

ORD record
ord-f0978a5bd0ef48dea4465673233ba6c3
Source dataset
uspto-grants-2006_11
Patent number
US07138411B2

Reaction notes

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