Acetic Anhydride → HCID 54227989, compound

HRID 1636317Notes

Reaction equation

HRID 1636317 reaction equation
C(OC(=O)C)(=O)C.[N:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]=[N:15][N:16]2[CH2:20][C:19](O)([CH3:21])[N:18]([N:23]=[CH:24][C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)[C:17]2=[O:31])[CH:9]=1.[OH-].[Na+]>C(O)(=O)C>[N:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]=[N:15][N:16]2[CH:20]=[C:19]([CH3:21])[N:18]([N:23]=[CH:24][C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)[C:17]2=[O:31])[CH:9]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 54567748HCID 54567748, compound

Product 1

HCID 54227989HCID 54227989, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

11.2 g of acetic anhydride are added to a suspension of 32.4 g of 1,3-bis(pyridin-3-yl-methyleneamino)-4-hydroxy-4-methylimidazolidin-2-one in 75 ml of acetic acid. The reaction mixture is then heated to 50°. After 3 hours the reaction mixture is cooled to 20°, then poured onto 800 ml of ice-water and neutralised with 30% sodium hydroxide solution. The aqueous phase is then extracted three times with 200 ml of methylene chloride each time. The organic phase is dried with magnesium sulfate, filtered and concentrated by evaporation. The residue is stirred with ether. The crystals are filtered off with suction and dried. 28.2 g of the title compound having a melting point of 176-178° are thus obtained.

Workup

  1. temperatureThe reaction mixture is then heated to 50°
  2. temperatureAfter 3 hours the reaction mixture is cooled to 20°
  3. extractionThe aqueous phase is then extracted three times with 200 ml of methylene chloride each time
  4. dry with materialThe organic phase is dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation
  7. filtrationThe crystals are filtered off with suction
  8. customdried
  9. customare thus obtained

Sources & evidence

ORD record
ord-5333a6a5dc314dcbb53cdf9652ae3380
Source dataset
uspto-grants-2000_03
Patent number
US06034083

Reaction notes

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