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

HRID 2392218Notes

Reaction equation

HRID 2392218 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([O:9]C)=[O:8])=[CH:4][C:3]=1[C:11]1[N:15]([CH3:16])[N:14]=[CH:13][C:12]=1[CH3:17].[OH-].[Na+]>O1CCCC1>[Cl:1][C:2]1[S:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][C:3]=1[C:11]1[N:15]([CH3:16])[N:14]=[CH:13][C:12]=1[CH3:17]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57826563methyl 5-chloro-4-(1,4-dimethyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate

Product 1

HCID 578264495-chloro-4-(1,4-dimethyl-1H-pyrazol-5-yl)-2-thiophenecarboxylic AcidYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a 100 mL round-bottomed flask was added methyl 5-chloro-4-(1,4-dimethyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate (106 mg, 0.39 mmol) in Tetrahydrofuran (THF) (2 mL). 6N NaOH (2 mL, 12.00 mmol) was added slowly and the reaction mixture stirred overnight at 70° C. The reaction was cooled to room temperature, partitioned between CHCl3 and H2O and the pH of the aqueous layer was adjusted to ˜3 by the addition of 6N HCl. The layers were separated, the organic layer dried over Na2SO4 and concentrated affording the desired compound (96 mg, 0.37 mmol, 95%): 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 was adjusted to ˜3 by the addition of 6N HCl
  4. customThe layers were separated
  5. dry with materialthe organic layer dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f6dc5a558bf64b53823c53b1c8f8ac00
Source dataset
uspto-grants-2012_09
Patent number
US08273782B2

Reaction notes

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