Benzaldehyde → HCID 19261677, compound

HRID 2295029Notes

Reaction equation

HRID 2295029 reaction equation
[NH:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6].[N:7]([O-])=O.[Na+].[CH:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>OS(O)(=O)=O.[Zn]>[C:12]1([CH:11]=[N:7][N:1]2[CH2:5][CH2:4][NH:3][C:2]2=[O:6])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 84532-ImidazolidinoneHCID 23668193Sodium Nitrite

Product 1

HCID 19261677HCID 19261677, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

A stirring solution of 65 g (0.75 mole) of 2-imidazolidinone in 2000 ml of 2N H2SO4 is cooled to 0° C. A 53 g (0.77 mole) portion of NaNO2 is added portionwise, over a 15 minute period, maintaining the temperature at 0° C. The resulting mixture is stirred at 0° C. for 2 hours. A 108 g (1.65 mole) portion of zinc dust is added portionwise, over a 1 hour period, maintaining the temperature at 0° C. The reaction is stirred at 0° C. for 0.5 hour and then at ambient temperature for 1 hour. The excess zinc is removed by filtration. The filtrate is treated all at once, with a solution of 80 g (0.75 mole) of benzaldehyde, in 400 ml of S.D.A. #32 and the resulting mixture is stirred hours at about 16 to 18 hours at ambient temperature. The solid is collected by filtration, washed with H2O, and air-dried to yield 124 g (87%) of 1-[(phenylmethylene)amino]-2-imidazolidinone.

Workup

  1. temperaturemaintaining the temperature at 0° C
  2. stirringThe reaction is stirred at 0° C. for 0.5 hour
  3. waitat ambient temperature for 1 hour
  4. customThe excess zinc is removed by filtration
  5. stirring#32 and the resulting mixture is stirred hours at about 16 to 18 hours at ambient temperature
  6. filtrationThe solid is collected by filtration
  7. washwashed with H2O
  8. customair-dried

Sources & evidence

ORD record
ord-a304f4c78e334e30bcb466cf802083c8
Source dataset
uspto-grants-1997_11
Patent number
US05691369

Reaction notes

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