Sodium Hydroxide → 4-(4-chloro-1-methyl-1H-pyrazol-5-yl)-5-methyl-2-furancarboxylic acid

HRID 2392205Notes

Reaction equation

HRID 2392205 reaction equation
C1C(=O)N([Cl:8])C(=O)C1.[CH3:9][C:10]1[O:14][C:13]([C:15]([O:17]C)=[O:16])=[CH:12][C:11]=1[C:19]1[N:23]([CH3:24])[N:22]=[CH:21][CH:20]=1.[OH-].[Na+]>O1CCCC1>[Cl:8][C:20]1[CH:21]=[N:22][N:23]([CH3:24])[C:19]=1[C:11]1[CH:12]=[C:13]([C:15]([OH:17])=[O:16])[O:14][C:10]=1[CH3:9]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 31398ChlorosuccinimideHCID 57826387methyl 5-methyl-4-(1-methyl-1H-pyrazol-5-yl)-2-furancarboxylate

Product 1

HCID 578264484-(4-chloro-1-methyl-1H-pyrazol-5-yl)-5-methyl-2-furancarboxylic acidYield 100.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

NCS (709 mg, 5.31 mmol) was added in portions to a 150 mL sealed tube reactor containing methyl 5-methyl-4-(1-methyl-1H-pyrazol-5-yl)-2-furancarboxylate (967 mg, 4.39 mmol) in Tetrahydrofuran (THF) (20 mL) at room temperature. The mixture was heated to 70° C. for 1 hour. 6N NaOH (20 mL, 120 mmol) was then added and the mixture stirred at 70° C. for an additional 2 h. The mixture was partitioned between CHCl3 and H2O and the pH of the aqueous phase was adjusted to ˜3 with 6N HCl. The organic layer was separated, dried with Na2SO4 and concentrated affording the title compound (1.13 g, 4.41 mmol, quant.) which was used without further purification: LC-MS (ES) m/z=241 (M+H)+.

Workup

  1. customsealed tube reactor
  2. customThe mixture was partitioned between CHCl3 and H2O
  3. customThe organic layer was separated
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0b1e45bbae124c9ba07d30ffe8922152
Source dataset
uspto-grants-2012_09
Patent number
US08273782B2

Reaction notes

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