Potassium Carbonate → HCID 43542552, compound

HRID 1748496Notes

Reaction equation

HRID 1748496 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][NH:9][CH:10]=1)=[O:5])C.I[C:12]1[CH:13]=[C:14]([CH3:19])[CH:15]=[C:16]([CH3:18])[CH:17]=1.CNC1CCCCC1NC.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.[Cu]I.O>[CH3:19][C:14]1[CH:13]=[C:12]([N:9]2[CH:10]=[C:6]([C:4]([OH:3])=[O:5])[CH:7]=[N:8]2)[CH:17]=[C:16]([CH3:18])[CH:15]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 1409241-Iodo-3,5-dimethylbenzeneHCID 142179ethyl 1H-pyrazole-4-carboxylateHCID 5510741-N,2-N-dimethylcyclohexane-1,2-diamine

Product 1

HCID 43542552HCID 43542552, compoundYield 28.5%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of 1H-pyrazole-4-carboxylic acid ethyl ester (1.65 g), 5-iodo-m-xylene (1.65 g), copper (I) iodide (68 mg), N,N′-dimethyl-1,2-cyclohexanediamine (222 mg) and potassium carbonate (2.06 g) in toluene (2 ml) was stirred at 110° C. for 48 hours. After completion of the reaction, water was added and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was dissolved in ethanol (10 ml), 1N aqueous solution of sodium hydroxide (10 ml) was added and the mixture was stirred at room temperature overnight. The reaction solution was concentrated by an evaporator, the aqueous solution was acidified by the addition of 1N hydrochloric acid aqueous solution and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated to give the titled compound (438 mg) as a dark brown solid.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in ethanol (10 ml)
  6. addition1N aqueous solution of sodium hydroxide (10 ml) was added
  7. concentrationThe reaction solution was concentrated by an evaporator
  8. additionthe aqueous solution was acidified by the addition of 1N hydrochloric acid aqueous solution
  9. extractionextracted with ethyl acetate
  10. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-f61f739861894edaaf88babe9e058a67
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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