Sodium Hydroxide → HCID 14500736, compound

HRID 2350899Notes

Reaction equation

HRID 2350899 reaction equation
Cl.[CH:2]1([NH:8][C:9]2[C:13]([C:14]([O:16]CC)=[O:15])=[C:12]([CH3:19])[NH:11][N:10]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[OH-].[Na+]>C(O)C.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH:2]1([NH:8][C:9]2[C:13]([C:14]([OH:16])=[O:15])=[C:12]([CH3:19])[NH:11][N:10]=2)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 14500702HCID 14500702, compound

Product 1

HCID 14500736HCID 14500736, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 702EthanolSolvent

Procedure

A solution of 2 g (0.007 mole) of 3-cyclohexylamino-5-methyl-1H-pyrazole-4-carboxylic acid, ethyl ester hydrochloride [1:1] in 30 mL of ethanol was treated with 5 mL of 50% sodium hydroxide solution, 20 mg of tetrabutylammonium bromide and stirred rapidly while heating at reflux. After 20 hr the reaction mixture was diluted with ice water, extracted with 6×100 mL of isopropyl ether, the pH adjusted to 7 with concentrated sulfuric acid and to pH 5.5 with 10 g of sodium dihydrogen phosphate. The fine precipitate was collected by filtration to give 0.6 g of beige power, mp 162°-163° C. (degasses).

Workup

  1. temperaturewhile heating
  2. temperatureat reflux
  3. extractionextracted with 6×100 mL of isopropyl ether
  4. filtrationThe fine precipitate was collected by filtration
  5. customto give 0.6 g of beige power, mp 162°-163° C. (degasses)

Sources & evidence

ORD record
ord-719c5b9361724787bb5bc3b2159344f2
Source dataset
uspto-grants-1989_10
Patent number
US04871737

Reaction notes

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