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

HRID 224506Notes

Reaction equation

HRID 224506 reaction equation
[Cl:1][C:2]1[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]([C:16](=O)[CH2:17][CH3:18])[C:12](=O)[CH2:13][CH3:14].O.[NH2:27][NH2:28]>C(O)C>[Cl:1][C:2]1[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[C:16]([CH2:17][CH3:18])=[N:27][NH:28][C:12]=1[CH2:13][CH3:14]

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 702EthanolSolvent

Procedure

A mixture of 18.5 g (0.05 m) of 4-[6-(2-chloro-4-methoxyphenoxy)hexyl]-3,5-heptanedione and 5 ml of 100% hydrazine hydrate in 100 ml of absolute ethanol was heated at reflux for five hours. The reaction mixture was concentrated in vacuo, the residue dissolved in 50 ml of ethanol, and the solution made acid with hydrochloric acid. The latter solution was concentrated in vacuo and the residue crystallized twice from an isopropyl alcohol-ether mixture to give 14.5 g of 4-[6-(2-chloro-4-methoxyphenoxy)hexyl]-3,5-diethyl-1H-pyrazole in the form of its hydrochloride salt, m.p. 117°-118° C. The corresponding hydrobromide salt had the m.p. 118°-120° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for five hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. dissolutionthe residue dissolved in 50 ml of ethanol
  5. concentrationThe latter solution was concentrated in vacuo
  6. customthe residue crystallized twice from an isopropyl alcohol-ether mixture

Sources & evidence

ORD record
ord-3f4787d5cbac42cdad5ebcb5acbde3b3
Source dataset
uspto-grants-1980_11
Patent number
US04232161

Reaction notes

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