Hydrazine → 2,2,4,5,5-Pentamethyl-2,5-dihydro-1H-imidazol-1-ol

HRID 1458270Notes

Reaction equation

HRID 1458270 reaction equation
[CH3:1][C:2]1[C:7]([CH3:9])([CH3:8])[N+:5](=[O:6])[C:4]([CH3:11])([CH3:10])[N:3]=1.NN.O.NN>CO>[OH:6][N:5]1[C:7]([CH3:9])([CH3:8])[C:2]([CH3:1])=[N:3][C:4]1([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 9321HydrazineHCID 24654Hydrazine hydrate (1:1)HCID 6422149HCID 6422149, compound

Product 1

HCID 3793702,2,4,5,5-Pentamethyl-2,5-dihydro-1H-imidazol-1-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.5 g (0.01 mole) of 2,2,4,5,5-pentamethyl-3-imidazoline-1-oxyl prepared as described in either of Examples 4 and 5 was solved in 10 ml methanol and treated with 1.5 ml (0.03 mole) of hydrazine or hydrazine-hydrate at ambient temperature. This solution was stored for 12 hours and over this period the methanol evaporated and the color of the solution disappeared. The partly crystallized residue was stirred with acetone and the colorless crystals were filtered and rinsed with acetone. 1.32 g of the isolated crystals with a yield of 88% were crystallized from ethyl acetate producing 1-hydroxy-2,2,4,5,5-pentamethyl-3-imidazoline having a melting point of 127°-128° C.

Workup

  1. customthe methanol evaporated
  2. filtrationthe colorless crystals were filtered
  3. washrinsed with acetone
  4. custom1.32 g of the isolated crystals with a yield of 88% were crystallized from ethyl acetate

Sources & evidence

ORD record
ord-d513de87d91746e4a08d148c33242ad2
Source dataset
uspto-grants-1998_12
Patent number
US05849929

Reaction notes

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