Water → HCID 178463810, compound

HRID 555958Notes

Reaction equation

HRID 555958 reaction equation
Cl.[NH2:2][NH:3][C:4]([NH2:6])=[O:5].C([O-])(=O)C.[Na+].[CH2:12]([N:14]([CH2:36][CH3:37])[C:15]1[CH:20]=[CH:19][C:18]([C:21](=O)[C:22]([C:24]2[CH:29]=[CH:28][C:27]([N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])=[CH:26][CH:25]=2)=O)=[CH:17][CH:16]=1)[CH3:13].O>C(O)(=O)C>[OH:5][C:4]1[N:3]=[N:2][C:21]([C:18]2[CH:19]=[CH:20][C:15]([N:14]([CH2:36][CH3:37])[CH2:12][CH3:13])=[CH:16][CH:17]=2)=[C:22]([C:24]2[CH:25]=[CH:26][C:27]([N:30]([CH2:31][CH3:32])[CH2:33][CH3:34])=[CH:28][CH:29]=2)[N:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11236Semicarbazide hydrochlorideHCID 517045Sodium AcetateHCID 4616522Ethanedione, bis[4-(diethylamino)phenyl]-

Product 1

HCID 178463810HCID 178463810, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Semicarbazide hydrochloride (1.57 g, 14.2 mmol) and sodium acetate (1.41 g, 17.3 mmol) are added to a solution of 1,2-bis(4-diethylaminophenyl)-ethane-1,2-dione prepared according to example 2 (5 g, 14.2 mmol) in acetic acid (20 ml). The mixture is heated at reflux for 12 hours. After returning to ambient temperature, the reaction mixture is poured into water. The raw solid is collected by filtration and washed with water. The residue is recrystallized in acetic acid. After filtration and washing with water, 3 g (54%) of a yellow solid are obtained after drying. δH (200 MHz, CDCl3), 1.18 (t; 12H), 3.45 (q; 8H), 6.65 (d; J 7.8; 4H), 7.87 (d; J 7.8; 4H), 10.4 (s; 1H)

Workup

  1. customprepared
  2. temperatureThe mixture is heated
  3. temperatureat reflux for 12 hours
  4. customAfter returning to ambient temperature
  5. filtrationThe raw solid is collected by filtration
  6. washwashed with water
  7. customThe residue is recrystallized in acetic acid
  8. filtrationAfter filtration
  9. washwashing with water, 3 g (54%) of a yellow solid
  10. customare obtained
  11. customafter drying

Sources & evidence

ORD record
ord-45c696a3da0c4c02b0beeca6a673a41f
Source dataset
uspto-grants-2011_11
Patent number
US08053573B2

Reaction notes

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