Water → HCID 178489128, compound

HRID 555960

Reaction equation

HRID 555960 reaction equation
[NH2:1][NH:2][C:3]([NH2:5])=[O:4].C([O-])(=O)C.[Na+].[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=O)[C:20]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)=O)=[CH:15][CH:14]=1.O>C(O)(=O)C>[OH:4][C:3]1[N:2]=[N:1][C:20]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)=[C:19]([C:16]2[CH:15]=[CH:14][C:13]([O:12][CH3:11])=[CH:18][CH:17]=2)[N:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5196SemicarbazideHCID 710434,4'-DimethoxybenzilHCID 517045Sodium Acetate

Product 1

HCID 178489128HCID 178489128, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Semicarbazide chlorohydrate (2.22 g, 20 mmol) and sodium acetate (1.80 g, 22 mmol) are added to a solution of 1,2-bis(4-methoxyphenyl)-ethane-1,2-dione (5.4 g, 20 mmol) prepared according to example 1 in acetic acid (25 ml). The mixture is heated at reflux for 12 hours. After returning to ambient temperature, the reaction mixture is poured into water. The raw reaction product is collected by filtration and washed with water. The residue is recrystallized in acetic acid. After filtration and washing in water, 5.9 g (95%) of a yellow solid is obtained after drying. δH (200 MHz, CDCl3), 3.86 (s; 6H), 6.94 (m; 4H), 7.67 (s; 4H).

Workup

  1. customprepared
  2. temperatureThe mixture is heated
  3. temperatureat reflux for 12 hours
  4. customAfter returning to ambient temperature
  5. customThe raw reaction product
  6. filtrationis collected by filtration
  7. washwashed with water
  8. customThe residue is recrystallized in acetic acid
  9. filtrationAfter filtration
  10. washwashing in water

Sources & evidence

ORD record
ord-d30614c92eb14bd9a914fd8da32fb25d
Source dataset
uspto-grants-2011_11
Patent number
US08053573B2

Linked notes

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