Hydrazine hydrate (1:1) → HCID 20333115, compound

HRID 426789Notes

Reaction equation

HRID 426789 reaction equation
O.[NH2:2][NH2:3].[C:4]([CH:8]([C:32](=[O:35])[CH2:33][CH3:34])[CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][CH:23]([C:28](=O)[CH2:29][CH3:30])[C:24](=O)[CH2:25][CH3:26])=[CH:15][CH:14]=1)(=[O:7])[CH2:5][CH3:6]>C(O)C>[C:4]([CH:8]([C:32](=[O:35])[CH2:33][CH3:34])[CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][C:23]2[C:28]([CH2:29][CH3:30])=[N:2][NH:3][C:24]=2[CH2:25][CH3:26])=[CH:15][CH:14]=1)(=[O:7])[CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 3007321HCID 3007321, compound

Product 1

HCID 20333115HCID 20333115, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 0.36 ml (0.00815 m) of hydrazine hydrate in 350 ml of ethanol was added dropwise during a 90 minute period to a solution of 3.3 g (0.0074 m) of 1,4-bis(4,4-dipropionylbutyloxy)benzene in 700 ml of ethanol held at 0°-5° C. and with vigorous stirring. The reaction mixture was then heated at reflux for 2.5 hours and allowed to stand at room temperature overnight. The reaction mixture was concentrated in vacuo, and the residue was treated with ethereal hydrogen chloride. The solid product which formed was collected and stirred for two hours with 250 ml boiling isopropyl acetate, then filtered and concentrated. The solid residue was recrystallized from isopropyl acetate to give 1.6 g of 4-{3-[4-(4,4-dipropionylbutyloxy)phenoxy]propyl}-3,5-diethyl-1H-pyrazole, m.p. 135°-136° C.

Workup

  1. customheld at 0°-5° C. and with vigorous stirring
  2. temperatureThe reaction mixture was then heated
  3. temperatureat reflux for 2.5 hours
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. additionthe residue was treated with ethereal hydrogen chloride
  6. customThe solid product which formed
  7. customwas collected
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe solid residue was recrystallized from isopropyl acetate

Sources & evidence

ORD record
ord-fe28861648e8406a87ce0b86bc44e86b
Source dataset
uspto-grants-1979_10
Patent number
US04171365

Reaction notes

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