Methanol → HCID 69500037, compound

HRID 2207947Notes

Reaction equation

HRID 2207947 reaction equation
C[O:2][C:3]([C:5]1[CH2:9][CH:8]([C:10]2[S:11][C:12]([Br:15])=[CH:13][CH:14]=2)[N:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])[N:6]=1)=[O:4].[OH-].[K+].CO>O>[Br:15][C:12]1[S:11][C:10]([CH:8]2[N:7]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])[N:6]=[C:5]([C:3]([OH:4])=[O:2])[CH2:9]2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 118432122HCID 118432122, compound

Product 1

HCID 69500037HCID 69500037, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

5-(5-Bromo-thiophen-2-yl)-1-(2-chloro-phenyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid methyl ester (18.9 g, 47.3 mmol) prepared in Step 3 and a solution of potassium hydroxide (5.3 g, 94.6 mmol) in distilled water (200.0 mL) were added to methanol (200.0 mL). The reaction mixture was stirred at 80° C. for 12 hours and then concentrated under reduced pressure to discard methanol. The resulting residue was washed with diethyl ether, acidified by a 1N hydrochloric acid solution, and then extracted with ethyl acetate. The extract was washed with distilled water and brine, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give 18.1 g of the titled compound as a pale yellow solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. washThe resulting residue was washed with diethyl ether
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with distilled water and brine
  5. dry with materialdried on anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4e2546411266489891ecc2fb23ba5922
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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