Acetic Anhydride → 4-[[4-Nitro-3-[(2,4-dioxoimidazolidin-5-ylidene)methyl]phenyl]oxy]butanoic acid

HRID 867471Notes

Reaction equation

HRID 867471 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19])[O:6][CH2:7][CH2:8][CH2:9][C:10]([O:12]CC)=[O:11])=O.[NH:21]1[CH2:27][C:25](=[O:26])[NH:24][C:22]1=[O:23].C([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C>O>[N+:18]([C:17]1[CH:16]=[CH:15][C:5]([O:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:4][C:3]=1[CH:1]=[C:27]1[NH:21][C:22](=[O:23])[NH:24][C:25]1=[O:26])([O-:20])=[O:19]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 10006HydantoinHCID 517045Sodium AcetateHCID 10588876Ethyl 4-((3-formyl-4-nitrophenyl)oxy)butyrate

Product 1

HCID 538103764-[[4-Nitro-3-[(2,4-dioxoimidazolidin-5-ylidene)methyl]phenyl]oxy]butanoic acidYield 37%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 4-[3-formyl-4-nitrophenoxy]butanoate (2.00 g, 7.1 mmol), hydantoin (0.71 g, 7.1 mmol), and anhydrous sodium acetate (0.58 g, 7.1 mmol) and acetic anhydride (20 mL) was heated at reflux for 1 hour. Upon cooling, H2O was added and the mixture extracted with dichloromethane. The organic portion was washed with water, evaporated, and the residue dissolved in a solution of methanol (20 mL) and 4N NaOH (30 mL). After stirring for 1 hour, the mixture was acidified to pH=2 by addition of 2N HCl. The precipitate was collected and triturated with MeOH/CH2Cl2 to afford 4-[[4-nitro-3-[(2,4-dioxoimidazolidin-5-ylidene)methyl]phenyl]oxy]butanoic acid (0.88 g, 37%). An analytical sample was prepared by crystallization from DMF/H2O to give gold plates, m.p. 181°-184° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. temperatureUpon cooling
  4. extractionthe mixture extracted with dichloromethane
  5. washThe organic portion was washed with water
  6. customevaporated
  7. dissolutionthe residue dissolved in a solution of methanol (20 mL) and 4N NaOH (30 mL)
  8. additionthe mixture was acidified to pH=2 by addition of 2N HCl
  9. customThe precipitate was collected
  10. customtriturated with MeOH/CH2Cl2

Sources & evidence

ORD record
ord-44d1472a7dcb445a8c53247d1559fced
Source dataset
uspto-grants-1988_10
Patent number
US04775674

Reaction notes

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