Acetic Anhydride → 4-[(2,5-Dioxoimidazolidin-4-ylidene)methyl]benzonitrile

HRID 274224Notes

Reaction equation

HRID 274224 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1)#[N:2].[NH:11]1[CH2:17][C:15](=[O:16])[NH:14][C:12]1=[O:13].C([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C>C(O)(=O)C>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[C:17]2[NH:11][C:12](=[O:13])[NH:14][C:15]2=[O:16])=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 10006HydantoinHCID 660424-CyanobenzaldehydeHCID 517045Sodium Acetate

Product 1

HCID 541420304-[(2,5-Dioxoimidazolidin-4-ylidene)methyl]benzonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

36.7 g (0.28 mol) of 4-cyanobenzaldehyde, 10 g (0.1 mol) of hydantoin, 21.6 g (0.263 mol) of sodium acetate and 28.6 ml (0.3 mol) of acetic anhydride are heated under reflux in 85 ml of acetic acid for 4 hours. After cooling, the mixture is poured onto ice and extracted with methylene chloride. The methylene chloride phase is concentrated, and the residue is stirred with methanol and filtered off with suction.

Workup

  1. temperatureAfter cooling
  2. additionthe mixture is poured onto ice
  3. extractionextracted with methylene chloride
  4. concentrationThe methylene chloride phase is concentrated
  5. filtrationfiltered off with suction

Sources & evidence

ORD record
ord-afeed6daf91b4b52bfee03ef4c2b5346
Source dataset
uspto-grants-1995_02
Patent number
US05389614

Reaction notes

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