Acetic Anhydride → HCID 54060171, compound

HRID 274222Notes

Reaction equation

HRID 274222 reaction equation
[CH3:1][N:2]1[CH2:6][C:5](=[O:7])[N:4]([CH2:8][C:9]([OH:11])=[O:10])[C:3]1=[O:12].[C:13]([C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1)#[N:14].C([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C>C(O)(=O)C>[C:13]([C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[C:6]2[N:2]([CH3:1])[C:3](=[O:12])[N:4]([CH2:8][C:9]([OH:11])=[O:10])[C:5]2=[O:7])=[CH:17][CH:16]=1)#[N:14]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 660424-CyanobenzaldehydeHCID 517045Sodium AcetateHCID 4962467(3-methyl-2,5-dioxo-1-imidazolidinyl)acetic acid(SALTDATA: H2O)

Product 1

HCID 54060171HCID 54060171, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2.6 g (15 mmol) of (1-methyl-2,4-dioxoimidazolidin-3-yl)-acetic acid, 2.9 g (22 mmol) of 4-cyanobenzaldehyde, 1.8 g (22 mmol) of sodium acetate and 2.1 ml (22 mmol) of acetic anhydride are heated under reflux in 25 ml of acetic acid for 6 hours. After cooling, the mixture is poured onto ice and extracted with ethyl acetate. The ethyl acetate phase is extracted with sodium bicarbonate solution and the aqueous phase is acidified. The product which has precipitated is filtered off with suction and dried.

Workup

  1. temperatureAfter cooling
  2. additionthe mixture is poured onto ice
  3. extractionextracted with ethyl acetate
  4. extractionThe ethyl acetate phase is extracted with sodium bicarbonate solution
  5. customThe product which has precipitated
  6. filtrationis filtered off with suction
  7. customdried

Sources & evidence

ORD record
ord-166aa2c231ef4b1eb92efb55bc155838
Source dataset
uspto-grants-1995_02
Patent number
US05389614

Reaction notes

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