Acetic Acid → HCID 86742234, compound

HRID 580249Notes

Reaction equation

HRID 580249 reaction equation
[Cl:1][C:2]1[C:3]([NH:11][NH2:12])=[C:4]([F:10])[S:5][C:6]=1[CH2:7][C:8]#[CH:9].CC[O:15][C:16]([CH:18]1[C:23](=O)[CH2:22][CH2:21][CH2:20][CH2:19]1)=O.C(O)(=O)C>O>[Cl:1][C:2]1[C:3]([N:11]2[C:16](=[O:15])[CH:18]3[C:19]([CH2:20][CH2:21][CH2:22][CH2:23]3)=[N:12]2)=[C:4]([F:10])[S:5][C:6]=1[CH2:7][C:8]#[CH:9]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 95543Ethyl 2-oxocyclohexanecarboxylateHCID 86742235HCID 86742235, compound

Product 1

HCID 86742234HCID 86742234, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-chloro-2-fluoro-5-propargylthiophenylhydrazine (1.2 g), ethyl 2-cyclohexanonecarboxylate (0.85 g) and acetic acid (10 ml) was heated under reflux for 2 hours, followed by cooling. Water was added thereto, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and a saturated sodium hydrogen carbonate solution, dried and concentrated. The residue was crystallized from a mixture of n-hexane and ether to give 0.87 g of 2-(4-chloro-2-fluoro-5-propargylthiophenyl)-3,3a,4,5,6,7-hexahydro-2H-indazol-3-one. M.P., 170°-171° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. temperatureby cooling
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materiala saturated sodium hydrogen carbonate solution, dried
  7. concentrationconcentrated
  8. customThe residue was crystallized from a mixture of n-hexane and ether

Sources & evidence

ORD record
ord-f8563b2487bb46a8be341325b50ef3cc
Source dataset
uspto-grants-1988_06
Patent number
US04752325

Reaction notes

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