Cyclohexanone → HCID 69477021, compound

HRID 1772182Notes

Reaction equation

HRID 1772182 reaction equation
[CH3:1][N:2]1[C:6]([NH2:7])=[CH:5][C:4]([CH:8]([CH3:10])[CH3:9])=[N:3]1.[C:11]1(=O)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>C(O)(=O)C>[CH3:1][N:2]1[C:6]([NH2:7])=[C:5]([C:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=2)[C:4]([CH:8]([CH3:10])[CH3:9])=[N:3]1

Participants

4

Reactant 2

HCID 7967CyclohexanoneHCID 27594993-Isopropyl-1-methyl-1H-pyrazol-5-amine

Product 1

HCID 69477021HCID 69477021, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Under nitrogen atmosphere, to a 100 mL of round bottom flask were added the compound of Example 2B (5.2 g, 38 mmol) and 40 mL of glacial acetic acid. After the compound was dissolved with stirring, cyclohexanone (8.22 g, 76 mmol) was added. The resultant mixture was warmed to 50° C. The reaction was kept overnight. The reaction was stopped. Glacial acetic acid was rotary-evaporated. The resultant product was dissolved with ethyl acetate and washed to alkalescence with aqueous solution of sodium bicarbonate. The ethyl acetate layer was separated. The aqueous layer was extracted twice with ethyl acetate. The organic layers were combined and dried over MgSO4. The solvent was rotary-evaporated. The product was purified with column chromatography (eluant: petroleum ether:ethyl acetate=1:1) to give 4.5 g of the title compound. MS (ESI): m/z 220 (M+H)+

Workup

  1. dissolutionAfter the compound was dissolved
  2. customGlacial acetic acid was rotary-evaporated
  3. dissolutionThe resultant product was dissolved with ethyl acetate
  4. washwashed
  5. customThe ethyl acetate layer was separated
  6. extractionThe aqueous layer was extracted twice with ethyl acetate
  7. dry with materialdried over MgSO4
  8. customThe solvent was rotary-evaporated
  9. customThe product was purified with column chromatography (eluant: petroleum ether:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-cc20d14130194198a545f6eaae3bd20e
Source dataset
uspto-grants-2016_02
Patent number
US09249172B2

Reaction notes

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