Sodium Hydroxide → 4-(3-chloro-1,4-dimethyl-1H-pyrazol-5-yl)-2-thiophenecarboxylic Acid

HRID 2392196Notes

Reaction equation

HRID 2392196 reaction equation
[Cl:1][C:2]1[C:6]([CH3:7])=[C:5]([C:8]2[CH:9]=[C:10]([C:13]([O:15]C)=[O:14])[S:11][CH:12]=2)[N:4]([CH3:17])[N:3]=1.[OH-].[Na+]>O1CCCC1>[Cl:1][C:2]1[C:6]([CH3:7])=[C:5]([C:8]2[CH:9]=[C:10]([C:13]([OH:15])=[O:14])[S:11][CH:12]=2)[N:4]([CH3:17])[N:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57826401methyl 4-(3-chloro-1,4-dimethyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate

Product 1

HCID 578264594-(3-chloro-1,4-dimethyl-1H-pyrazol-5-yl)-2-thiophenecarboxylic AcidYield 66.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a 100 mL round-bottomed flask was added methyl 4-(3-chloro-1,4-dimethyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate (2.15 g, 7.94 mmol) in Tetrahydrofuran (THF) (30 ml). 6N NaOH (30 mL, 180 mmol) was added slowly and the reaction stirred at 70° C. overnight. The reaction was cooled to room temperature, partitioned between CHCl3 and H2O and the pH of the aqueous layer adjusted to ˜3 by the addition of 6N HCl. The layers were separated, the organic layer dried with Na2SO4 and solvent removed affording the title compound (1.35 g, 5.26 mmol, 66%) which was used in the next step without further purification LC-MS (ES) m/z=257 (M+H)+.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. custompartitioned between CHCl3 and H2O
  3. additionthe pH of the aqueous layer adjusted to ˜3 by the addition of 6N HCl
  4. customThe layers were separated
  5. dry with materialthe organic layer dried with Na2SO4 and solvent
  6. customremoved

Sources & evidence

ORD record
ord-c597fadb4aa44e7a8b635accb4b28be0
Source dataset
uspto-grants-2012_09
Patent number
US08273782B2

Reaction notes

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