Acetic Acid → HCID 23453299, compound

HRID 1277724Notes

Reaction equation

HRID 1277724 reaction equation
[NH:1]([C:3]1[CH:13]=[CH:12][C:6]([O:7][CH2:8][C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1)[NH2:2].[C:14](N1C2N(C(=O)C)C(=O)N(C(=O)C)C2N(C(=O)C)C1=O)(=[O:16])[CH3:15].C(O)(=O)C>C(#N)C.C(O)C>[C:14]([NH:2][NH:1][C:3]1[CH:4]=[CH:5][C:6]([O:7][CH2:8][C:9]([OH:11])=[O:10])=[CH:12][CH:13]=1)(=[O:16])[CH3:15]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 827171,3,4,6-Tetraacetyltetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dioneHCID 23453300HCID 23453300, compound

Product 1

HCID 23453299HCID 23453299, compoundYield 122.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

4-Hydrazinophenoxyacetic acid 0.1H2O (10.0 g) and 1,3,4,6-tetraacetyltetrahydroimidazo[4,5-d]imidazole-2,5-(1H,3H)-dione (7.8 g) were suspended in dry acetonitrile (200 ml) containing acetic acid (1 ml). The mixture was heated under reflux for 3 hours, cooled to room temperature, and filtered. The precipitate was washed well with acetonitrile; the washings were combined with the filtrate, and this solution was evaporated to give a dark oil. The residue was taken up in hot ethanol (25 ml) and the brownn powder which precipitated on chilling was filtered off and dried. Recrystallization from acetonitrile gave the product as chunky, tan crystals (6.9 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. filtrationfiltered
  4. washThe precipitate was washed well with acetonitrile
  5. customthis solution was evaporated
  6. customto give a dark oil
  7. customthe brownn powder which precipitated
  8. temperatureon chilling
  9. filtrationwas filtered off
  10. customdried
  11. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-6d93c2f4fbdf4ae382e709d1f3cdf4a6
Source dataset
uspto-grants-1981_07
Patent number
US04278748

Reaction notes

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