Hydrazine hydrate (1:1) → 4-(6-(2-Chloro-4-methoxyphenoxy)hexyl)-3,5-diethyl-1H-pyrazole

HRID 224938Notes

Reaction equation

HRID 224938 reaction equation
O.[NH2:2][NH2:3].[Cl:4][C:5]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:6]=1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]([C:19](=O)[CH2:20][CH3:21])[C:15](=O)[CH2:16][CH3:17]>CO>[Cl:4][C:5]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:6]=1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]1[C:19]([CH2:20][CH3:21])=[N:2][NH:3][C:15]=1[CH2:16][CH3:17]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 41782Arildone

Product 1

HCID 1554474-(6-(2-Chloro-4-methoxyphenoxy)hexyl)-3,5-diethyl-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydrazine hydrate (15.7 ml, 0.32 m) was added over a 20 min. period to a slurry of 100 g (0.272 m) of 4-[6-(2-chloro-4-methoxyphenoxy)hexyl]-3,5-heptanedione in 300 ml of methanol. The internal temperature rose to a maximum of 50° C. during the addition. The reaction mixture was heated at reflux for one hour, and the solvent was then removed in vacuo. The residue was dissolved in 300 ml of methylene dichloride and the resulting solution was washed with three 100 ml portions of water. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated to leave 100 g of 4-[6-(2-chloro-4-methoxyphenoxy)hexyl]-3,5-diethyl-1H-pyrazole as a colorless oil.

Workup

  1. additionThe internal temperature rose to a maximum of 50° C. during the addition
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for one hour
  4. customthe solvent was then removed in vacuo
  5. dissolutionThe residue was dissolved in 300 ml of methylene dichloride
  6. washthe resulting solution was washed with three 100 ml portions of water
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-4b66c73538634c7d8227b728f3780b8a
Source dataset
uspto-grants-1980_11
Patent number
US04234725

Reaction notes

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